ࡱ> s w<jbjb Ƥkkw8]RRRRR,~4Ru ;;;2 4 4 4 4 4 4 ,_ S ` ;";;;` S;(2 TT;2 S2 RRc(* Acids and Bases Skill List link to each section below Vocabulary Conjugate Acids and Bases Use of the pKa Table Molecular Structure and Acidity Vocabulary Discussion: Words in chemistry often have very precise meanings that are meant to convey specific concepts or relationships. It is important for you to be able to define these words in a precise and accurate manner, and provide examples where relevant. Understanding is much more useful than rote memorization. Exercises: Provide a precise definition for each word. Acid ionization constant Bronsted-Lowry acid Bronsted-Lowry base Conjugate acid Conjugate base Inductive effect Lewis acid Lewis base pKa link to exercise solutions Conjugate Acid and Bases Discussion: Proton transfers are key features of many organic and biochemical reactions. If a reactant accepts a proton (a Bronsted-Lowry base) the product is termed the conjugate acid of that base. An electron pair from the Bronsted-Lowry base is shared with the proton to make a new bond. If a reactant donates a proton (a Bronsted-Lowry acid), the product is the conjugate base of that acid. The electron pair that was the bond to the transferred proton is left behind as part of the conjugate base. As a fundamental skill necessary to master proton trasnfer reactions, you will need to be able to draw the conjugates of an acid or base. Example 1: Provide the products of the following proton transfer reaction. The proton that is transferred is circled. Label all reactants and products as Bronsted-Lowry or conjugate acids and bases.  Solution:  Example 2: A small portion of the molecules in liquid water have reacted by proton transfer. This process is termed autoionization. Write an equation for the autoionization of water that clearly illustrates this proton transfer. Name all the products. Label all reactants and products as Bronsted-Lowry or conjugate acids and bases. Solution:  Note that some compounds such as water in this example can function as either an acid or base. Such compounds are termd amphoteric. Where a compound is an acid or base is not controlled solely by molecular structure, but rather by the molecules role in the reaction. Exercises: Provide the products of each proton transfer reactions shown below. In each case, the proton that is transferred is circled. Label all reactants and products as Bronsted-Lowry or conjugate acids and bases.     e. The following proton transfer involves two steps. Can you figure out the structure of intermediates A and B?  Use of the pKa Table Discussion: The propensity of a compound to donate a proton is measured as its acid ionization constant, or Ka. These Ka values cover a wide range of 1010 for the strongest acids to 10-50 for the weakest acids. A more convenient scale of acidity is pKa which is the negative logarithm of the Ka. Thus a Ka of 1010 becomes a pKa of -10, and a Ka of 1050 becomes a pKa of -50. More generally, more negative pKa values correspond to stronger acids and more positive pKa values correspond to weaker acids. The exact pKa of an acid is a function of molecular structure (i.e., functional groups) and must be determined experimentally. We know that similar functional groups react in similar ways, so we can estimate pKa values by comparing the structure and functional groups of an unknown with the structure and functional groups of acids whose pKa values are known. Example: By comparison with the compounds in Table 2.1 (page 43) of the text, estimate the pKa of the following compounds. a. CH3CH2CH2CO2H (butyric acid) b. CH3OH2+ (an oxonium ion). Solution: a. Butyric acid is similar in structure to CH3CO2H (acetic acid), in that both are carboxylic acids. The pKa of acetic acid is 4.78. Therefore we can estimate the pKa of butyric acid to be approximately 4 - 5. b. The closest structural match for the oxonium ion in the pKa table is the hydronium ion (H3O+), pKa -1.74. Thus we can estimate the pKa of CH3OH2+ to be approximately -2. The pKa table is also useful to estimate the position of a proton transfer equilibrium. Such reactions are common in many aspects of chemistry and biology. Any equilibrium favors the thermodynamically most stable side. In the case of a proton transfer reaction, the equilibrium favors the side with the weakest acid and weakest base. Because a stronger conjugate acid yields a weaker conjugate base, base strength can be determined from the pKa table. Example: Determine the position of the equilibrium shown below.  Solution: This is a proton transfer equilibrium, so the position can be determined using pKa values. The acids (proton donors) in this equilibrium are H2CO3 (carbonic acid, pKa 6.36) and NH4+ (ammonium ion, pKa 9.24). The ammonium ion has the higher pKa of the two, and is therefore a weaker acid than carbonic acid. To analyze relative basicity, we need to recall that lower pKa corresponds to a stronger acid, and deprotonation of this stronger acid will give a weaker conjugate base. The bases (proton acceptors) in this equilibrium are NH3 (ammonia; conjugate acid NH4+, pKa 9.24) and HCO3- (bicarbonate ion; conjugate acid H2CO3, pKa 6.36). From the fact that H2CO3 is a stronger acid than NH4+,we can deduce that HCO3- is a weaker base than NH3.  Analysis of the relative acid and base strengths suggests that this equilibrium lies to the right. Exercises: Estimate the pKa of the circled hydrogens.  d. Determine the most acidic hydrogen in the compound shown below.  Determine the position of each of the following equilibria.    --link to exercise solutions-- Molecular Structure and Acidity Discussion: There are approximately ten millions of known compounds, but only 17 are listed in Table 2.1. Even the most extensive pKa tables include only a few thousand compounds. How can we know the pKa of a compound that is not on such a table? There are certainly many situations in which it would be impractical to synthesize the compound just to measure its pKa (such as during an exam!). We have seen before that because similar functional groups react in similar ways that compounds with similar functional groups will have similar pKa values. We can use this fact as a basis to predict trends in acidity or basicity. Recall that the role of a base is to share an electron pair with a proton, resulting in a new bond to that proton. A molecule that can donate electrons more readily will therefore be a stronger base. (There are some additional factors that we will not consider at this level.) Because we know that stronger bases have weaker conjugate acids, we can apply this same analysis to determine acidity as well. Many factors can influence a molecules ability to donate electrons. The most common factors are electronegativity, resonance, and the inductive effect. We consider each of these below. (These same factors also influence nucleophilicity, a topic studied in section 7.4A of the text.) Electronegativity: Recall that electronegativity is the measure of an atoms attraction for electrons. The higher the electronegativity, the greater the attraction. We can extend this idea further and conclude that atoms with higher electronegativity will be less inclined to share there electrons with a proton. Thus, increasing electronegativity of the atom that shares an electron pair will decrease basicity. Since weaker bases have stronger conjugate acids, we can conclude that as the electronegativity of the atom bearing the proton increases, the acidity of that proton also increases. Electronegativity values can be found Table 1.5 (page 7) of the text. The most commonly used scale was devised by Linus Pauling. On the Pauling scale, fluorine has the highest electronegativity (4.0) and cesium has the lowest (0.7). Electronegativity values generally do not need to be memorized, as study of Table 1.5 reveals a simple trend. As we move further away from fluorine on the periodic table, electronegativity decreases. The exception to this is the noble gasses, which have essentially zero electronegativity.  Example: Rank the following compounds in order of increasing acidity without using a pKa table: CH4, NH3, H2O, HF. Solution: Convert each acid to its conjugate base, and consider the ability of that conjugate base to share an electron pair. The conjugate bases are:  The lone pairs that are shared with a proton reside on C, N, O, and F. Of these, carbon is the least electronegative (most willing to share electrons), so CH3- would be the strongest base. Fluorine is the most electronegative, so F- would be the least willing to donate electrons (the weakest base). Overall, the electronegativity order is C (2.5) < N (3.0) < O (3.5) < F (4.0), so the order of basicity is: CH3- (strongest base) > NH2- > HO- > F-. The relationship between conjugate basicity and acidity is an inverse one, so the order of acidity is: CH4 (weakest acid) < NH3 < H2O < HF (strongest acid). The actual pKa values agree: CH4 pKa 51 (weakest acid), NH3 pKa 38, H2O pKa 15.7, HF pKa 3.5. Resonance: A molecule is said to have resonance when more than one Lewis structure can be drawn for that molecule. How does resonance influence the ability of a base to share electrons with a proton? In the case of a base bearing a negative charge, resonance may delocalize this charge, increasing the stability of the base. Greater stability results in lower reactivity. A base that has resonance delocalization of the charge or the electron pair that is shared with the proton will therefore be less basic than a base without this feature. Since a weaker base has a stronger conjugate acid, a compound who conjugate base enjoys resonance stabilization will be more acidic. Example: Which is more acidic, ethanol (CH3CH2OH) or acetic acid (CH3CO2H)? Solution: Acidity can readily be analyzed by examining the corresponding conjugate bases:  Deprotonation of ethanol affords ethoxide ion, which has no resonance (only one Lewis structure can be drawn). Deprotonation of acetic acid affords acetate ion which has resonance (two contributing Lewis structures can be drawn). Because acetate ion has resonance and ethoxide ion does not, acetate ion is a weaker base than ethoxide ion. Recalling that weaker bases have stronger conjugate bases, we conclude that acetic acid is a stronger acid than ethanol. The actual pKa values agree with our prediction. For acetic acid the pKa is 4.76 (stronger acid) and for ethanol the pKa is 15.9 (weaker acid). The resonance effect on pKa can be viewed in a variety of ways. For example, we can consider the magnitude of the charge on the atom(s) that would share an electron pair with a proton. An atom with greater charge has a higher incentive to stabilize this charge by sharing a pair of electrons with a proton. Thus, everything else being equal, an ion with more net charge per atom that shares an electron pair is a stronger base. Examination of the resonance hybrid structure for acetate ion suggests that the charge on each oxygen atom that would share an electron pair with a proton is -1/2. The charge on the oxygen of ethoxide ion is -1. Because each oxygen of acetate ion has a smaller charge, it has less incentive to stabilize this charge by sharing an electron pair. Less incentive to share an electron pair with a hydrogen means lowers basicity.  Alternately, recall that stability tends to increase with an increasing number of significant contributing resonance structures. Protonation usually results in loss of one or more of these resonance structures. A base with many resonance structures stands to lose more resonance than a base with a lesser number of resonance structures. Thus a base with many resonance structures will resist protonation (be a poorer base) than a similar structure with fewer resonance structures. Acetate ion has two contributing resonance structures, and has more to lose upon protonation than ethoxide with a single resonance structure. This analysis suggests acetate ion to be a poorer base than ethoxide ion, and thus acetic acid to be a stronger acid than ethanol. Inductive effect: We have seen the effect of differences in the electronegativity or charge of the atom that shares a pair of electrons with a proton. What effect on basicity is seen when the structural differences are not limited to the atom sharing the electron pair? Example: What is the effect on the acidity of acetic acid (CH3CO2H) when one of the methyl group hydrogens is replaced by a chlorine atom to make chloroacetic acid (ClCH2CO2H)? Alternately, what does this do to the relative basicity of acetate ion (CH3CO2-) versus chloroacetate ion (ClCH2CO2-)? Solution: This structural difference does not change the electronegativity of the oxygen atoms that share an electron pair with a proton, nor does it change the number of contributing resonance structures. A new explanation is in order. Recall that the role of a base is to share an electron pair with a proton. The less electron density available (i.e. less negative charge), the harder it is for the atom to share this electron pair. What effect does the replacement of hydrogen with chlorine have on the oxygens electron density? Chlorine is more electronegative than oxygen, so the chlorine pulls electron density from the adjacent carbon atom. This carbon atom in turn borrows electron density from the neighboring carbonyl carbon, and so forth. The end effect is that the chlorine atom pulls electron density toward itself and away from the CO2- (carboxylate) group. The reduced electron density of the carboxylate group means lower basicity. Thus we predict ClCH2CO2- to be a poorer base than CH3CO2-, and by extension, ClCH2CO2H to be a stronger acid than CH3CO2H. The actual pKa values are 2.86 for ClCH2CO2H (stronger acid) and 4.76 for CH3CO2H (weaker acid). (You can read more about the inductive effect and the pKa of carboxylic acids in section 8.4A, page 212 of the text.) The effect of one atom or group of atoms on the electron density on a remote portion of the molecule is called the inductive effect. Exercises: Without relying on a pKa table, rank each set of compounds in order of decreasing acidity. 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ac 0 Y lp Y lp ac X lp s 0 p M X 0 X Y lp ac X Y 2 dv X lp a o lp ac X Y 2 dv X Y lp ac X Y X lp s Y lp ac SM st}{Y D 2 dv Y 180 pA s 180 pA a arc st np X Y s Y 2 dv Y pA D neg arcn st}{Rc SM st}{X lW 2 dv a lW -2 dv p M rO D rlineto X lW 2 dv a rO a Y lW 2 dv a rO a p l rO lW -2 dv a Y lW 2 dv a rO a p l lW -2 dv Y lW 2 dv a p l 0 Y p l X Y p l X 0 p l cp f 0 0 p M 0 Y p l X Y p l X 0 p l cp SM st}{Rr SM st}{rO Y p M rO rO xl 0 Y X Y rO ac X Y X 0 rO ac X 0 0 0 rO ac rO neg D xl X Y 0 Y rO ac cp f Rr st}{Ac st}{OrA gAc}{Ov st}{OrA 1 .4 sc gOv}{Asc LB whf}{Asc gLB}{Asc gs gLB gr -1 -1 sc LB whf}{Asc gs gLB gr -0.4 -0.4 sc LB whf}{Asc LB gs whf gr np -0.4 -0.4 sc gLB}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro gs gDLB gr -1 -1 sc gDLB}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc gOv gr ZLB whf}{Asc gs -1 -1 sc gZLB gr gs 3.6 12 sc Cr whf gr gZLB}{0 0 p M X Y p l SM st}{bW sl 0 0 p M X Y p l SM st}{dL 0 0 p M X Y p l SM st}{OrA 1 16 dv D sc 0 -1 p M 0 0 1 0 1 ac 8 0 8 1 1 ac 8 0 16 0 1 ac 16 0 16 -1 1 ac SM st}{XY D 0 0 dt X Y dt}{XY 2 dv X Y dt}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l 2 0 M 0 0 2 0 360 arc Ast}{4.5 Aos 1 0 M -1 0 l 2 0 M 0 0 2 0 360 arc Ast}{2.25 Ath}{1.5 Ath}{1 Ath}{2.25 Aeq}{1.5 Aeq}{1 Aeq}{OrA 1 16 dv D sc 0 -1 p M 0 0 p l 16 0 p l 16 -1 p l SM st}{5 Aos 1 -1 M -1 -1 l 0 2 M 0 -2 l Ast}{5 Aos 1 -1 M -1 -1 l 1 1 M -1 1 l 0 2 M 0 -2 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{4.5 Aos 1 0 M -1 0 l Ast}{gRc}{gRr}{Rc blf}{Rr blf}{Ac blf}{Ov blf}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro DLB -1 -1 sc DLB blf}{Asc gs -1 -1 sc ZLB blf gr gs 3.6 12 sc Cr whf gr ZLB blf}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc Cr blf gr ZLB whf}{Asc LB gs whf gr np -0.4 -0.4 sc LB blf}{Asc LB gs f gr gs SM st gr np -0.4 -0.4 sc LB whf}{Asc LB blf}{Asc LB gs f gr gs SM st gr np -1 -1 sc LB whf}{Ac whf}{OrA gAc}{Ac blf}{Ov whf}{OrA 1 .4 sc gOv}{Ov blf}}e 39 s g xc gr}ie}b/DS{np p M p l st}b/DD{gs dL DS gr}b/DB{gs 12 OB bW sl np 0 0 p M 0 p l st gr}b/ap{e 3 ix a e 2 ix a}b/PT{D 2 4 gi al P OP D 1 sc o length 6 gt{P 6 g}{e P 8 dv}ie D lW 2 m lt{P lW 2 m}if 0 e p 0 0 p 3 -1 r s 3 1 r e s e 0 0 p M 1 0 p l 0 0 p ap M 1 0 p ap l e n e n 0 0 p ap M 1 0 p ap l P P}b/DT{gs np PT SM st gr}b O/NH{lW s D hS dv ru cvi D 0 eq{P 1}if/nH x D hS nH m s D 0 lt{P .1 s nH dv}{nH 2 a dv D 0 xl 2 m s nH dv}ie}b/Bd{D type/arraytype ne{bs e g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b "`F"`H"x9# "w_Q\^QWYQq\t^QqWtYQ[?^BQV?YBQ[M^PQVMYPQehQehqkqnqnkn"mPhewt"c"c"{ # Q02Q+-Qt0w2Qt+w-Q^aQY\Q^!a$QY!\$Q~57Qy5|7Po6x?"s8QpsQkn"loPeXtgQevhyQeqhtQrvuyQrqutql_wdwbl_nbmdwb"la"ga"aa"\a"Wa"Qa"LaQtwQtwP_h"cq]hh]_^h"]"X"R"M"H end %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 381 125 24 35 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 1394 1910 M 1414 1910 l 1414 2245 l 1394 2245 l cp f np 1446 1910 M 1466 1910 l 1466 2245 l 1446 2245 l cp f np 1142 2408 M 1132 2390 l 1430 2218 l 1430 2242 l cp f np 1675 2360 M 1665 2378 l 1430 2242 l 1430 2218 l cp f np 1915 2394 M 1905 2376 l 2045 2295 l 2055 2313 l cp f 1864 2570 1764 2570 62 Ar 1864 2290 1764 2290 62 Ar 1290 1850 1290 1750 62 Ar 1570 1850 1570 1750 62 Ar 3670 2050 3570 2050 62 Ar 4950 2190 4110 2190 2 Ar 2178 2370 2178 2230 46 Ar np 5634 1970 M 5654 1970 l 5654 2305 l 5634 2305 l cp f np 5686 1970 M 5706 1970 l 5706 2305 l 5686 2305 l cp f np 5382 2468 M 5372 2450 l 5670 2278 l 5670 2302 l cp f np 5915 2420 M 5905 2438 l 5670 2302 l 5670 2278 l cp f 6104 2630 6004 2630 62 Ar 6104 2350 6004 2350 62 Ar 5530 1910 5530 1810 62 Ar 5810 1910 5810 1810 62 Ar 6194 2550 6194 2450 62 Ar 6270 2290 6270 2490 67 Ar 3510 2270 3510 2170 62 Ar np 7340 2160 M 7340 2180 l 7120 2180 l 7120 2160 l cp f 7030 2310 7030 2170 46 Ar 7510 2050 7410 2050 62 Ar 7510 2310 7410 2310 62 Ar 1950 2370 1950 1510 20 Ar 3670 2350 3570 2350 62 Ar 3870 1970 3870 2170 67 Ar 3610 2070 3610 1370 20 Ar gr count origstk sub{P}rp end chemsave restore ,Times .+D^O(~$H *+ 3 (~1C)%O(thH(aO(H *+ 3 (C)%O(qI+ H)(OH(s ) OH( proton donor * Bronsted-Lowry acid( proton acceptor * Bronsted-Lowry base(Mconjugate acid(r+(-&The bonding electron pair *  is left behind when the *  proton is transferred.(3 One lone pair on oxygen * becomes the new O-H bond.+HRconjugate basedCHMDSTRG#  x (P6>d R >dR>dD>dD,,>d `  $d$h>d  %>d 8` 8 eH`. L>d P P~>d 8 8~ >d!>d">d < <#C $. +>d ` ,>d ` -\ LdC((f * 0L0  & 0'   (O H3CHOO H3C + H O OH ` `PPX `   L (` a  2 p4  `   `   @ f `  $ t d ` 4 `  $V) |V  ` 4<H `  4k\ < OH%   l x X % proton donor Bronsted-Lowry acid'    m x X' proton acceptor Bronsted-Lowry base   ht t conjugate base   Tq  |conjugate acid   r\  |+N   4NThe bonding electron pair is left behind when the proton is transferred.3   \ t3 One lone pair on oxygen becomes the new O-H bond.Times' ;swsD Timesx! D4D! D4Da Timesx '(! DD& TimesxH3C^! DcD Timesx ' '! D@D Timesx '( L L8  ! E1D! E1Dh Timesx ' (! E%D& TimesxH3C^! E=`D Timesx '  ' ! E\D@& Timesx + H^! EiD@ TimesxOH '( p  8T 8T .Hok\ <\ < OHļĤĜ        @ < x X x X % proton donor Bronsted-Lowry acidļĤĜ                                        @ Z< R x X x X' proton acceptor Bronsted-Lowry baseļĤĜ                                          @ Zz6  |  |conjugate acidļĤĜ  <               @ x.[W\  |\  |+ļĤĜ    @ |r ,V  NThe bonding electron pair is left behind when the proton is transferred.ļĤĜ  <                                                                               @ RUQ\ t\ t3 One lone pair on oxygen becomes the new O-H bond.ļĤĜ                                                      @ d2@ t  t conjugate baseļĤĜ  <               @;D6* ,T S&WordMicrosoft Word&Word 9  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. 9: :CHMD:GrphbjdCHMDacids and bases_strdCHMD ,, ` #),, `,-^&'count  89 :currentpoint 192837465 !: currentpoint  :": save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 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54 d/pA 32 d/sh F d/S{sf m}b/dL{[hS] 0 setdash}b/o{1 ix}b/rot{3 -1 r}b/x{e d}b/CMT mt d/TM mt d/SM{CMT sm}b/XY{X D m Y D m a sq}b/s1 1 string d/fp{T charpath flattenpath}b/p{tr ru 0.25 a e ru 0.25 a e itransform}b/C{65536. dv rot 65536. dv rot 65536. dv rot setrgbcolor}b/sg{D currenthsbcolor P rot sethsbcolor currenthsbcolor e P e P o s D m .001 gt{setgray}{P}ie}b/sBg{65535 dv/bBg x 65535 dv/gBg x 65535 dv/rBg x}b/sRmp{currentrgbcolor bBg e s/bDst x gBg e s/gDst x rBg e s/rDst x}b/N 0 d/db{array/bs x/N 0 d}b/B{bs N rot put/N N 1 a d}b/SpA{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie aR aL m n D aL a 0 p M 0 o n aA n aA arc cp f gr}b/SpH{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie 0 cw 2 dv xl aR aL m n D aL a 0 p M 0 o n aA n 0 arc cp f gr}b/Sp{/St x 0.316/aR x gs aF lW m 0.8 m St 4 and 0 ne{bW m lW dv bW sl}if/aL x St 8 and 0 ne{8 ix 8 ix 3 ix 3 ix SpA}if St 16 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpA}if St 32 and 0 ne{8 ix 8 ix 3 ix 3 ix SpH}if St 64 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpH}if St 2 and 0 ne{St 4 and 0 ne{[hS bW m lW dv] 0 setdash}{dL}ie}if np M{cv}rp St 128 and 0 ne{f}{st}ie gr}b/Ha{gs np 3 1 r xl D sc -.7 1.4 p M 0.7 1.4 p l -.7 2.4 p M 0.7 2.4 p l SM st gr}b/OP{3 ix 3 ix xl 3 -1 r s 3 1 r e s o o at ro D m e D m a sq}b/OB{/bS x OP D bS dv D lW 2 m lt{P lW 2 m}if/bd x}b/DA{np 0 0 M aL 0 aR aL m 180 aA s 180 aA a arc cp f}b/OA{np 0 cw -2 dv M aL 0 aR aL m 180 aA s 180 arc 0 cw -2 dv rlineto cp f}b/Ast{SM cw 0.8 m sl st}b/SA{aF m lW m/aL x 0.263/aR x aL 1 aR s m np 0 p M rad 0 p l gs Ast gr}b/CA{aF lW m 0.8 m/aL x 0.316/aR x aL 1 aR s m 2 dv rad D m o D m s D 0 le{P P P}{sq at 2 m np rad 0 rad 180 6 -1 r s 180 6 -1 r s arc gs Ast gr cpt e at ro}ie}b/AA{np rad 0 rad 180 180 6 -1 r a arc gs SM st gr}b/RA{lW m/w x np rad w p M w .7 dv w p l rad w n p M w .7 dv w n p l w .35 dv w 2 m p M 0 0 p l w .35 dv w -2 m p l st}b/HA{lW m/w x np 0 0 p M w 2 m D p l w 2 m w p l rad w p l rad w n p l w 2 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e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b "+Q#%Q#%Q35Q35Q-e/gQ(e*gQ-/Q(*P#}4q).+.+)+"+end %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 178 28 47 286 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 2980 5970 M 2980 5990 l 2770 5990 l 2770 5970 l cp f 3220 5840 3120 5840 62 Ar 3192 6160 3092 6160 62 Ar 2040 6040 2040 5940 62 Ar 3300 6040 3300 5940 62 Ar 2660 6140 2660 5980 46 Ar 4444 5980 3480 5980 2 Ar gr count origstk sub{P}rp end chemsave restore ,Times .(/H)Cl(/1a.) (CH *+3 (/U) +3 )(/^N +dCHMDSTRG/:  x (P6>d  0t>d x u>d4v>d 4 w. d\ dx\\\ y\ dn\ opHCl `  D   `  L    4`a. `   L (CH3)3N +Times'swsD Timesx! D@E: Timesx! DE: Timesx '(  T     8  v `\4`4`a.ļĤĜ     @ b  b  L  L (CH3)3N +ļĤĜ  4             @.D4 S&WordMicrosoft Word&Word b-  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. -bR1 1RCHMDR1GrphbjdCHMDacids and bases_strdCHMD ,, ` #),, `,-^&'count  P/Q0 R1currentpoint 192837465 !R1 currentpoint  R1"H1 save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform L/xl/translate L/xc/exec L/A R/N R/St R/X R/Y R/aL R/bL R/bS R/bd R/bs R/cX R/cY R/ch R/co R/fB R/fI R/fS R/fZ R/fl R/ft R/iX R/iY R/idx R/lh R/llx R/lly R/lp R/nH R/nSq R/newdict R/ps R/rad R/rev R/sL R/sba R/sbl R/sbs R/sn R/spa R/tB R/typ R/urx R/ury R/w R/wF R/xX R/xY R/rBg R/gBg R/bBg R/gry R/rDst R/gDst R/bDst R/cpd R/sf 20 d/cW 20 d/lW 20 d/bW 75 d/wF 1.5 d/aF 11.875 d/aR 0.263 d/aA 50 d/hS 54 d/pA 32 d/sh F d/S{sf m}b/dL{[hS] 0 setdash}b/o{1 ix}b/rot{3 -1 r}b/x{e d}b/CMT mt d/TM mt d/SM{CMT sm}b/XY{X D m Y D m a sq}b/s1 1 string d/fp{T charpath flattenpath}b/p{tr ru 0.25 a e ru 0.25 a e itransform}b/C{65536. dv rot 65536. dv rot 65536. dv rot setrgbcolor}b/sg{D currenthsbcolor P rot sethsbcolor currenthsbcolor e P e P o s D m .001 gt{setgray}{P}ie}b/sBg{65535 dv/bBg x 65535 dv/gBg x 65535 dv/rBg x}b/sRmp{currentrgbcolor bBg e s/bDst x gBg e s/gDst x rBg e s/rDst x}b/N 0 d/db{array/bs x/N 0 d}b/B{bs N rot put/N N 1 a 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sc gZLB gr gs 3.6 12 sc Cr whf gr gZLB}{0 0 p M X Y p l SM st}{bW sl 0 0 p M X Y p l SM st}{dL 0 0 p M X Y p l SM st}{OrA 1 16 dv D sc 0 -1 p M 0 0 1 0 1 ac 8 0 8 1 1 ac 8 0 16 0 1 ac 16 0 16 -1 1 ac SM st}{XY D 0 0 dt X Y dt}{XY 2 dv X Y dt}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l 2 0 M 0 0 2 0 360 arc Ast}{4.5 Aos 1 0 M -1 0 l 2 0 M 0 0 2 0 360 arc Ast}{2.25 Ath}{1.5 Ath}{1 Ath}{2.25 Aeq}{1.5 Aeq}{1 Aeq}{OrA 1 16 dv D sc 0 -1 p M 0 0 p l 16 0 p l 16 -1 p l SM st}{5 Aos 1 -1 M -1 -1 l 0 2 M 0 -2 l Ast}{5 Aos 1 -1 M -1 -1 l 1 1 M -1 1 l 0 2 M 0 -2 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{4.5 Aos 1 0 M -1 0 l Ast}{gRc}{gRr}{Rc blf}{Rr blf}{Ac blf}{Ov blf}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro DLB -1 -1 sc DLB blf}{Asc gs -1 -1 sc ZLB blf gr gs 3.6 12 sc Cr whf gr ZLB blf}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc Cr blf gr ZLB whf}{Asc LB gs whf gr np -0.4 -0.4 sc LB blf}{Asc LB gs f gr gs SM st gr np -0.4 -0.4 sc LB whf}{Asc LB blf}{Asc LB gs f gr gs SM st gr np -1 -1 sc LB whf}{Ac whf}{OrA gAc}{Ac blf}{Ov whf}{OrA 1 .4 sc gOv}{Ov blf}}e 39 s g xc gr}ie}b/DS{np p M p l st}b/DD{gs dL DS gr}b/DB{gs 12 OB bW sl np 0 0 p M 0 p l st gr}b/ap{e 3 ix a e 2 ix a}b/PT{D 2 4 gi al P OP D 1 sc o length 6 gt{P 6 g}{e P 8 dv}ie D lW 2 m lt{P lW 2 m}if 0 e p 0 0 p 3 -1 r s 3 1 r e s e 0 0 p M 1 0 p l 0 0 p ap M 1 0 p ap l e n e n 0 0 p ap M 1 0 p ap l P P}b/DT{gs np PT SM st gr}b O/NH{lW s D hS dv ru cvi D 0 eq{P 1}if/nH x D hS nH m s D 0 lt{P .1 s nH dv}{nH 2 a dv D 0 xl 2 m s nH dv}ie}b/Bd{D type/arraytype ne{bs e g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b "z<# "`M"`P"gQ[H^JQVHYJQ[V^XQVVYXP_pqekhkheh"g9end %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 202 45 49 338 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 1211 7575 M 1201 7557 l 1580 7338 l 1580 7362 l cp f np 1959 7557 M 1949 7575 l 1580 7362 l 1580 7338 l cp f np 1544 7030 M 1564 7030 l 1564 7365 l 1544 7365 l cp f np 1596 7030 M 1616 7030 l 1616 7365 l 1596 7365 l cp f np 3180 7180 M 3180 7200 l 2970 7200 l 2970 7180 l cp f 1460 6970 1460 6870 62 Ar 1740 6970 1740 6870 62 Ar 2860 7350 2860 7190 46 Ar 4964 7190 4000 7190 2 Ar gr count origstk sub{P}rp end chemsave restore ,Times .(^KO+@H)OSO +3 (lH(k3b.+8+dCHMDSTRGR1  x (P6>dD>dD. , , d ,z{, , |}~OHOSO3H ` `MX| ` p R p | ` p X d  \\b.  p\\p+VTimes'swsD Timesx! DEEf! DEl! DuEl ' '! DEEX@ Timesx '(! DEa Timesx! D@Ea TimesxOSO3H '( < j  8  ~`\\\b.ļĤĜ     @ . ~[W\p\p+ļĤĜ    @,Dd  S&WordMicrosoft Word&Word T+  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. +T2 2CHMD2GrphbjdCHMDacids and bases_strdCHMD ,, ` #),, `,-^&'count  01 2currentpoint 192837465 !2 currentpoint  2"2 save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub 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0 p M X Y p l SM st}{bW sl 0 0 p M X Y p l SM st}{dL 0 0 p M X Y p l SM st}{OrA 1 16 dv D sc 0 -1 p M 0 0 1 0 1 ac 8 0 8 1 1 ac 8 0 16 0 1 ac 16 0 16 -1 1 ac SM st}{XY D 0 0 dt X Y dt}{XY 2 dv X Y dt}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l 2 0 M 0 0 2 0 360 arc Ast}{4.5 Aos 1 0 M -1 0 l 2 0 M 0 0 2 0 360 arc Ast}{2.25 Ath}{1.5 Ath}{1 Ath}{2.25 Aeq}{1.5 Aeq}{1 Aeq}{OrA 1 16 dv D sc 0 -1 p M 0 0 p l 16 0 p l 16 -1 p l SM st}{5 Aos 1 -1 M -1 -1 l 0 2 M 0 -2 l Ast}{5 Aos 1 -1 M -1 -1 l 1 1 M -1 1 l 0 2 M 0 -2 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{4.5 Aos 1 0 M -1 0 l Ast}{gRc}{gRr}{Rc blf}{Rr blf}{Ac blf}{Ov blf}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro DLB -1 -1 sc DLB blf}{Asc gs -1 -1 sc ZLB blf gr gs 3.6 12 sc Cr whf gr ZLB blf}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc Cr blf gr ZLB whf}{Asc LB gs whf gr np -0.4 -0.4 sc LB blf}{Asc LB gs f gr gs SM st gr np -0.4 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sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b "ZqZiZZiiZ"i qi{{{ii{"y"|"P"PQZ"S"Uq"q'11'('1"&"IqIXIIXXI"X qXjjjXXj"h"k"xQend %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 330 56 66 145 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 1807 3375 M 1797 3357 l 2090 3188 l 2090 3212 l cp f np 2464 3404 M 2464 3428 l 2090 3212 l 2090 3188 l cp f np 2428 3401 M 2448 3401 l 2448 3710 l 2428 3710 l cp f np 2480 3401 M 2500 3401 l 2500 3710 l 2480 3710 l cp f np 2705 3265 M 2715 3283 l 2464 3428 l 2464 3404 l cp f 2974 3060 2974 3260 67 Ar 1696 3220 1696 3420 66 Ar 4074 3560 3110 3560 2 Ar 6094 3560 5130 3560 2 Ar np 6587 3435 M 6577 3417 l 6870 3248 l 6870 3272 l cp f np 7244 3464 M 7244 3488 l 6870 3272 l 6870 3248 l cp f np 7208 3461 M 7228 3461 l 7228 3770 l 7208 3770 l cp f np 7260 3461 M 7280 3461 l 7280 3770 l 7260 3770 l cp f np 7511 3310 M 7521 3328 l 7244 3488 l 7244 3464 l cp f gr count origstk sub{P}rp end chemsave restore ,Times .+DH *+ 3 (QN+&O(O+H *+ 2 (@N(A *)  + )B+rO(yOH(H *+ 2 (OdCHMDSTRGB  x (P6C B  \  &    * X    ` X DL  L ! "  H3NO H2NOO OH `   P  ` X P LP  `   H$ `   `  ( b `  r lt   O  8r |8 A + B+ `  \ $ H2O+Times'swsD Timesx! D@D! DWD& Timesx%! DD ' '! DD Timesx '(! DD Timesx ' 8  8! EWD! EK Dـ& Timesx%! Eb@Dـ '  '  > ^l |8 |8 A + BļĤĜ  (          @! Eb@D Timesx ' (! En D Timesx% '  ^ :ea  H2OļĤĜ      @,D0 S&WordMicrosoft Word&Word z+  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. +z{? ?{CHMD{?GrphbjdCHMDacids and bases_strdCHMD ,, ` #),, `,-^&'count  y=z> {?currentpoint 192837465 !{? currentpoint  {?"q? save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform L/xl/translate L/xc/exec L/A R/N R/St R/X R/Y R/aL R/bL R/bS R/bd R/bs R/cX R/cY R/ch R/co R/fB R/fI R/fS R/fZ R/fl R/ft R/iX R/iY R/idx R/lh R/llx R/lly R/lp R/nH R/nSq R/newdict R/ps R/rad R/rev R/sL R/sba R/sbl R/sbs R/sn R/spa R/tB R/typ R/urx R/ury R/w R/wF R/xX R/xY R/rBg R/gBg R/bBg R/gry R/rDst R/gDst R/bDst R/cpd R/sf 20 d/cW 20 d/lW 20 d/bW 75 d/wF 1.5 d/aF 11.875 d/aR 0.263 d/aA 50 d/hS 54 d/pA 32 d/sh F d/S{sf m}b/dL{[hS] 0 setdash}b/o{1 ix}b/rot{3 -1 r}b/x{e d}b/CMT mt d/TM mt d/SM{CMT sm}b/XY{X D m Y D m a sq}b/s1 1 string d/fp{T charpath flattenpath}b/p{tr ru 0.25 a e ru 0.25 a e itransform}b/C{65536. dv rot 65536. dv rot 65536. dv rot setrgbcolor}b/sg{D currenthsbcolor P rot sethsbcolor currenthsbcolor e P e P o s D m .001 gt{setgray}{P}ie}b/sBg{65535 dv/bBg x 65535 dv/gBg x 65535 dv/rBg x}b/sRmp{currentrgbcolor bBg e s/bDst x gBg e s/gDst x rBg e s/rDst x}b/N 0 d/db{array/bs x/N 0 d}b/B{bs N rot put/N N 1 a d}b/SpA{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie aR aL m n D aL a 0 p M 0 o n aA n aA arc cp f gr}b/SpH{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie 0 cw 2 dv xl aR aL m n D aL a 0 p M 0 o n aA n 0 arc cp f gr}b/Sp{/St x 0.316/aR x gs aF lW m 0.8 m St 4 and 0 ne{bW m lW dv bW sl}if/aL x St 8 and 0 ne{8 ix 8 ix 3 ix 3 ix SpA}if St 16 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpA}if St 32 and 0 ne{8 ix 8 ix 3 ix 3 ix SpH}if St 64 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpH}if St 2 and 0 ne{St 4 and 0 ne{[hS bW m lW dv] 0 setdash}{dL}ie}if np M{cv}rp St 128 and 0 ne{f}{st}ie gr}b/Ha{gs np 3 1 r xl D sc -.7 1.4 p M 0.7 1.4 p l -.7 2.4 p M 0.7 2.4 p l SM st gr}b/OP{3 ix 3 ix xl 3 -1 r s 3 1 r e s o o at ro D m e D m a sq}b/OB{/bS x OP D bS dv D lW 2 m lt{P lW 2 m}if/bd x}b/DA{np 0 0 M aL 0 aR aL m 180 aA s 180 aA a arc cp f}b/OA{np 0 cw -2 dv M aL 0 aR aL m 180 aA s 180 arc 0 cw -2 dv rlineto cp f}b/Ast{SM cw 0.8 m sl st}b/SA{aF m lW m/aL x 0.263/aR x aL 1 aR s m np 0 p M rad 0 p l gs 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p l X lp s 0 p M X 0 p l X Y p l X lp s Y p l SM st}{Y 16 div D 2 S lt{P 2 S}if/lp x lp 0 p M 0 0 0 Y lp ac 0 Y 2 dv lp neg o lp ac 0 Y 2 dv 0 Y lp ac 0 Y lp Y lp ac X lp s 0 p M X 0 X Y lp ac X Y 2 dv X lp a o lp ac X Y 2 dv X Y lp ac X Y X lp s Y lp ac SM st}{Y D 2 dv Y 180 pA s 180 pA a arc st np X Y s Y 2 dv Y pA D neg arcn st}{Rc SM st}{X lW 2 dv a lW -2 dv p M rO D rlineto X lW 2 dv a rO a Y lW 2 dv a rO a p l rO lW -2 dv a Y lW 2 dv a rO a p l lW -2 dv Y lW 2 dv a p l 0 Y p l X Y p l X 0 p l cp f 0 0 p M 0 Y p l X Y p l X 0 p l cp SM st}{Rr SM st}{rO Y p M rO rO xl 0 Y X Y rO ac X Y X 0 rO ac X 0 0 0 rO ac rO neg D xl X Y 0 Y rO ac cp f Rr st}{Ac st}{OrA gAc}{Ov st}{OrA 1 .4 sc gOv}{Asc LB whf}{Asc gLB}{Asc gs gLB gr -1 -1 sc LB whf}{Asc gs gLB gr -0.4 -0.4 sc LB whf}{Asc LB gs whf gr np -0.4 -0.4 sc gLB}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro gs gDLB gr -1 -1 sc gDLB}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc gOv gr ZLB whf}{Asc gs -1 -1 sc gZLB gr gs 3.6 12 sc Cr whf gr gZLB}{0 0 p M X Y p l SM st}{bW sl 0 0 p M X Y p l SM st}{dL 0 0 p M X Y p l SM st}{OrA 1 16 dv D sc 0 -1 p M 0 0 1 0 1 ac 8 0 8 1 1 ac 8 0 16 0 1 ac 16 0 16 -1 1 ac SM st}{XY D 0 0 dt X Y dt}{XY 2 dv X Y dt}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l 2 0 M 0 0 2 0 360 arc Ast}{4.5 Aos 1 0 M -1 0 l 2 0 M 0 0 2 0 360 arc Ast}{2.25 Ath}{1.5 Ath}{1 Ath}{2.25 Aeq}{1.5 Aeq}{1 Aeq}{OrA 1 16 dv D sc 0 -1 p M 0 0 p l 16 0 p l 16 -1 p l SM st}{5 Aos 1 -1 M -1 -1 l 0 2 M 0 -2 l Ast}{5 Aos 1 -1 M -1 -1 l 1 1 M -1 1 l 0 2 M 0 -2 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{4.5 Aos 1 0 M -1 0 l Ast}{gRc}{gRr}{Rc blf}{Rr blf}{Ac blf}{Ov blf}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro DLB -1 -1 sc DLB blf}{Asc gs -1 -1 sc ZLB blf gr gs 3.6 12 sc Cr whf gr ZLB blf}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc Cr blf gr ZLB whf}{Asc LB gs whf gr np -0.4 -0.4 sc LB blf}{Asc LB gs f gr gs SM st gr np -0.4 -0.4 sc LB whf}{Asc LB blf}{Asc LB gs f gr gs SM st gr np -1 -1 sc LB whf}{Ac whf}{OrA gAc}{Ac blf}{Ov whf}{OrA 1 .4 sc gOv}{Ov blf}}e 39 s g xc gr}ie}b/DS{np p M p l st}b/DD{gs dL DS gr}b/DB{gs 12 OB bW sl np 0 0 p M 0 p l st gr}b/ap{e 3 ix a e 2 ix a}b/PT{D 2 4 gi al P OP D 1 sc o length 6 gt{P 6 g}{e P 8 dv}ie D lW 2 m lt{P lW 2 m}if 0 e p 0 0 p 3 -1 r s 3 1 r e s e 0 0 p M 1 0 p l 0 0 p ap M 1 0 p ap l e n e n 0 0 p ap M 1 0 p ap l P P}b/DT{gs np PT SM st gr}b O/NH{lW s D hS dv ru cvi D 0 eq{P 1}if/nH x D hS nH m s D 0 lt{P .1 s nH dv}{nH 2 a dv D 0 xl 2 m s nH dv}ie}b/Bd{D type/arraytype ne{bs e g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b P""P"q"q" *end %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 224 28 63 635 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C 4080 12860 4080 13060 66 Ar 5580 12880 5580 13080 67 Ar 3960 13020 3000 13020 23 Ar 2980 13100 3340 13100 23 Ar gr count origstk sub{P}rp end chemsave restore ,Times .(ANH +3 U(W + H +!2 D(}CO +3 (NH +4 U( + HCO o+83d0CHMDSTRG{?  x (P62x2 B2<3C2P3h3, 3,  ` 3h23 ,NH3 + H2CO3 ` 3T23NH4 + HCO3Times'swsD Timesx d@23 ,23 ,NH3 + H2CO3ļĤĜ  @                @ Z.62323NH4 + HCO3ļĤĜ  D                 @ nn8 81Db q\8 S&WordMicrosoft Word&Word /  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. /{6! 6{!CHMD{6!GrphbjdCHMDacids and bases_strdCHMD ,, ` #),, `,-^&'count  y4z5 {6!currentpoint 192837465 !{6 currentpoint  {6!"q6 save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform L/xl/translate L/xc/exec L/A R/N R/St R/X R/Y R/aL R/bL R/bS R/bd R/bs R/cX R/cY R/ch R/co R/fB R/fI R/fS R/fZ R/fl R/ft R/iX R/iY R/idx R/lh R/llx R/lly R/lp R/nH R/nSq R/newdict R/ps R/rad R/rev R/sL R/sba R/sbl R/sbs R/sn R/spa R/tB R/typ R/urx R/ury R/w R/wF R/xX R/xY R/rBg R/gBg R/bBg R/gry R/rDst R/gDst R/bDst R/cpd R/sf 20 d/cW 20 d/lW 20 d/bW 75 d/wF 1.5 d/aF 11.875 d/aR 0.263 d/aA 50 d/hS 54 d/pA 32 d/sh F d/S{sf m}b/dL{[hS] 0 setdash}b/o{1 ix}b/rot{3 -1 r}b/x{e d}b/CMT mt d/TM mt d/SM{CMT sm}b/XY{X D m Y D m a sq}b/s1 1 string d/fp{T charpath flattenpath}b/p{tr ru 0.25 a e ru 0.25 a e itransform}b/C{65536. dv rot 65536. dv rot 65536. dv rot setrgbcolor}b/sg{D currenthsbcolor P rot sethsbcolor currenthsbcolor e P e P o s D m .001 gt{setgray}{P}ie}b/sBg{65535 dv/bBg x 65535 dv/gBg x 65535 dv/rBg x}b/sRmp{currentrgbcolor bBg e s/bDst x gBg e s/gDst x rBg e s/rDst x}b/N 0 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cp f}b/Ast{SM cw 0.8 m sl st}b/SA{aF m lW m/aL x 0.263/aR x aL 1 aR s m np 0 p M rad 0 p l gs Ast gr}b/CA{aF lW m 0.8 m/aL x 0.316/aR x aL 1 aR s m 2 dv rad D m o D m s D 0 le{P P P}{sq at 2 m np rad 0 rad 180 6 -1 r s 180 6 -1 r s arc gs Ast gr cpt e at ro}ie}b/AA{np rad 0 rad 180 180 6 -1 r a arc gs SM st gr}b/RA{lW m/w x np rad w p M w .7 dv w p l rad w n p M w .7 dv w n p l w .35 dv w 2 m p M 0 0 p l w .35 dv w -2 m p l st}b/HA{lW m/w x np 0 0 p M w 2 m D p l w 2 m w p l rad w p l rad w n p l w 2 m w n p l w 2 m D n p l cp st}b/Ar1{gs 5 1 r OP/rad x{{2.25 SA DA}{1.5 SA DA}{1 SA DA}{lW 4 m sl 4.5 SA DA}{lW 4 m sl 3 SA DA}{lW 4 m sl 2 SA DA}{270 CA DA}{180 CA DA}{120 CA DA}{90 CA DA}{2.5 RA}{2.5 HA}{1 -1 sc 270 CA DA}{1 -1 sc 180 CA DA}{1 -1 sc 120 CA DA}{1 -1 sc 90 CA DA}{5 RA}{5 HA}{dL 2.25 SA DA}{dL 1.5 SA DA}{dL 1 SA DA}{2.25 SA OA}{1.5 SA OA}{1 SA OA}{1 -1 sc 2.25 SA OA}{1 -1 sc 1.5 SA OA}{1 -1 sc 1 SA OA}{270 CA OA}{180 CA OA}{120 CA OA}{90 CA OA}{1 -1 sc 270 CA OA}{1 -1 sc 180 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whf gr gs 3.6 12 sc gOv gr ZLB whf}{Asc gs -1 -1 sc gZLB gr gs 3.6 12 sc Cr whf gr gZLB}{0 0 p M X Y p l SM st}{bW sl 0 0 p M X Y p l SM st}{dL 0 0 p M X Y p l SM st}{OrA 1 16 dv D sc 0 -1 p M 0 0 1 0 1 ac 8 0 8 1 1 ac 8 0 16 0 1 ac 16 0 16 -1 1 ac SM st}{XY D 0 0 dt X Y dt}{XY 2 dv X Y dt}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l 2 0 M 0 0 2 0 360 arc Ast}{4.5 Aos 1 0 M -1 0 l 2 0 M 0 0 2 0 360 arc Ast}{2.25 Ath}{1.5 Ath}{1 Ath}{2.25 Aeq}{1.5 Aeq}{1 Aeq}{OrA 1 16 dv D sc 0 -1 p M 0 0 p l 16 0 p l 16 -1 p l SM st}{5 Aos 1 -1 M -1 -1 l 0 2 M 0 -2 l Ast}{5 Aos 1 -1 M -1 -1 l 1 1 M -1 1 l 0 2 M 0 -2 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{4.5 Aos 1 0 M -1 0 l Ast}{gRc}{gRr}{Rc blf}{Rr blf}{Ac blf}{Ov blf}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro DLB -1 -1 sc DLB blf}{Asc gs -1 -1 sc ZLB blf gr gs 3.6 12 sc Cr whf gr ZLB blf}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc Cr blf gr ZLB whf}{Asc LB gs whf gr np -0.4 -0.4 sc LB blf}{Asc LB gs f gr gs SM st gr np -0.4 -0.4 sc LB whf}{Asc LB blf}{Asc LB gs f gr gs SM st gr np -1 -1 sc LB whf}{Ac whf}{OrA gAc}{Ac blf}{Ov whf}{OrA 1 .4 sc gOv}{Ov blf}}e 39 s g xc gr}ie}b/DS{np p M p l st}b/DD{gs dL DS gr}b/DB{gs 12 OB bW sl np 0 0 p M 0 p l st gr}b/ap{e 3 ix a e 2 ix a}b/PT{D 2 4 gi al P OP D 1 sc o length 6 gt{P 6 g}{e P 8 dv}ie D lW 2 m lt{P lW 2 m}if 0 e p 0 0 p 3 -1 r s 3 1 r e s e 0 0 p M 1 0 p l 0 0 p ap M 1 0 p ap l e n e n 0 0 p ap M 1 0 p ap l P P}b/DT{gs np PT SM st gr}b O/NH{lW s D hS dv ru cvi D 0 eq{P 1}if/nH x D hS nH m s D 0 lt{P .1 s nH dv}{nH 2 a dv D 0 xl 2 m s nH dv}ie}b/Bd{D type/arraytype ne{bs e g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b P""P"q"q"*end %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 235 54 54 635 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C 4070 12860 4070 13060 66 Ar 5570 12880 5570 13080 67 Ar 3950 13020 2990 13020 23 Ar 2970 13100 3330 13100 23 Ar gr count origstk sub{P}rp end chemsave restore ,Times .(ANH +3 U(W + H +!2 D(}CO +3 (NH +4 U( + HCO o+83 (8 stronger *  base(m stronger *  acid(weaker *  acid(weaker *  based$CHMDSTRG{6!  x (P62x2 B2<3C2P3h3, 3,  ` 3h23 ,NH3 + H2CO3 ` 3T23NH4 + HCO3  4`4`5l stronger base  445  stronger acid  4<3<5 weaker acid  435l weaker baseVTimes'wswsD Timesd d@23 ,23 ,NH3 + H2CO3ļĤĜ  @                @ Z.62323NH4 + HCO3ļĤĜ  D                 @ 0<4`5l4`5lstronger baseļĤĜ  D                 @ BN45 45 stronger acidļĤĜ  D                 @  Z3<53<5 weaker acidļĤĜ  8              @  35l35l weaker baseļĤĜ  8              @ nn8 88D5! S&WordMicrosoft Word&Word r7  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. 7r*N *NCHMD*NGrphbjdCHMDacids and bases_str2dCHMD ,, ` #),, `,-^&'count  () *Ncurrentpoint 192837465 !* currentpoint  *N" * save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform L/xl/translate L/xc/exec L/A R/N R/St R/X R/Y R/aL R/bL R/bS R/bd R/bs R/cX R/cY R/ch R/co R/fB R/fI R/fS R/fZ R/fl R/ft R/iX R/iY R/idx R/lh R/llx R/lly R/lp R/nH R/nSq R/newdict R/ps R/rad R/rev R/sL R/sba R/sbl R/sbs R/sn R/spa R/tB R/typ R/urx R/ury R/w R/wF R/xX R/xY R/rBg R/gBg R/bBg R/gry R/rDst R/gDst R/bDst R/cpd R/sf 20 d/cW 20 d/lW 20 d/bW 75 d/wF 1.5 d/aF 11.875 d/aR 0.263 d/aA 50 d/hS 54 d/pA 32 d/sh F d/S{sf m}b/dL{[hS] 0 setdash}b/o{1 ix}b/rot{3 -1 r}b/x{e d}b/CMT mt d/TM mt d/SM{CMT sm}b/XY{X D m Y D m a sq}b/s1 1 string d/fp{T charpath flattenpath}b/p{tr ru 0.25 a e ru 0.25 a e itransform}b/C{65536. dv rot 65536. dv rot 65536. dv rot setrgbcolor}b/sg{D currenthsbcolor P rot sethsbcolor currenthsbcolor e P e P o s D m .001 gt{setgray}{P}ie}b/sBg{65535 dv/bBg x 65535 dv/gBg x 65535 dv/rBg x}b/sRmp{currentrgbcolor bBg e s/bDst x gBg e s/gDst x rBg e s/rDst x}b/N 0 d/db{array/bs x/N 0 d}b/B{bs N rot put/N N 1 a d}b/SpA{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie aR aL m n D aL a 0 p M 0 o n aA n aA arc cp f gr}b/SpH{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie 0 cw 2 dv xl aR aL m n D aL a 0 p M 0 o n aA n 0 arc cp f gr}b/Sp{/St x 0.316/aR x gs aF lW m 0.8 m St 4 and 0 ne{bW m lW dv bW sl}if/aL x St 8 and 0 ne{8 ix 8 ix 3 ix 3 ix SpA}if St 16 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpA}if St 32 and 0 ne{8 ix 8 ix 3 ix 3 ix SpH}if St 64 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpH}if St 2 and 0 ne{St 4 and 0 ne{[hS bW m lW dv] 0 setdash}{dL}ie}if np M{cv}rp St 128 and 0 ne{f}{st}ie gr}b/Ha{gs np 3 1 r xl D sc -.7 1.4 p M 0.7 1.4 p l -.7 2.4 p M 0.7 2.4 p l SM st gr}b/OP{3 ix 3 ix xl 3 -1 r s 3 1 r e s o o at ro D m e D m a sq}b/OB{/bS x OP D bS dv D lW 2 m lt{P lW 2 m}if/bd x}b/DA{np 0 0 M aL 0 aR aL m 180 aA s 180 aA a arc cp f}b/OA{np 0 cw -2 dv M aL 0 aR aL m 180 aA s 180 arc 0 cw -2 dv rlineto cp f}b/Ast{SM cw 0.8 m sl st}b/SA{aF m lW m/aL x 0.263/aR x aL 1 aR s m np 0 p M rad 0 p l gs Ast gr}b/CA{aF lW m 0.8 m/aL x 0.316/aR x aL 1 aR s m 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1686 5347 l 1668 5337 l cp f np 1701 4657 M 1713 4637 l 1928 5010 l 1922 5020 l 1910 5020 l cp f np 1282 4657 M 1270 4637 l 1713 4637 l 1701 4657 l cp f np 1306 4709 M 1306 4689 l 1677 4689 l 1677 4709 l cp f np 1270 4637 M 1282 4657 l 1072 5020 l 1048 5020 l cp f np 2240 5010 M 2240 5030 l 1928 5030 l 1922 5020 l 1928 5010 l cp f 2620 4820 2620 5020 67 Ar 5020 5020 4280 5020 73 Ar np 5402 5384 M 5390 5404 l 5168 5020 l 5192 5020 l cp f np 5435 5337 M 5417 5347 l 5231 5025 l 5249 5015 l cp f np 5821 5384 M 5833 5404 l 5390 5404 l 5402 5384 l cp f np 6030 5020 M 6042 5020 l 6048 5030 l 5833 5404 l 5821 5384 l cp f np 5973 5015 M 5991 5025 l 5806 5347 l 5788 5337 l cp f np 5821 4657 M 5833 4637 l 6048 5010 l 6042 5020 l 6030 5020 l cp f np 5402 4657 M 5390 4637 l 5833 4637 l 5821 4657 l cp f np 5426 4709 M 5426 4689 l 5797 4689 l 5797 4709 l cp f np 5390 4637 M 5402 4657 l 5192 5020 l 5168 5020 l cp f np 6360 5010 M 6360 5030 l 6048 5030 l 6042 5020 l 6048 5010 l cp f 8260 4840 8260 5040 67 Ar gr count origstk sub{P}rp end chemsave restore ,Times .+rCO ++2 ( )CO ++2 (UH(+e. +l+ H +3 o(PO +4 (k+ D)  H +2 o(PO +4dCHMDSTRG)  x (P6C < <dIeC D Dw$UVWX'Y'Z 2a<ghij'k'lJs[\]^_`b t r q p o nmCO2 CO2H ` PL(  ` QL(0  \~L\e. `  L ( + H3PO4 H ` \L\(  + H2PO4@Times'swsD Timesx! DE! D E(! DTE(! DpE! DTE! D E '.( ' '.( ' '.( '! DE TimesxCO2  '  \ 8! E!E! E(E(! E5E(! E<E! E5E! E(E '.( ' '.( ' '.( '! EJE Timesx%CO2H< ! EJE! EQ`E! ECE(! EJE4 '(( ' ' '! EJE" 34CO2H6= '  : jfL\L\e. ļĤĜ       @  L (L ( + H3PO4ļĤĜ  ,           @ . R L\( L\( + H2PO4ļĤĜ  0            @B0D 0 S&WordMicrosoft Word&Word .  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. .w wCHMDwGrphbjdCHMDacids and bases_str2dCHMD ,, ` #),, `,-^&'count  uv wcurrentpoint 192837465 !w currentpoint  w"m save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform L/xl/translate L/xc/exec L/A R/N R/St R/X R/Y R/aL R/bL R/bS R/bd R/bs R/cX R/cY R/ch R/co R/fB R/fI R/fS R/fZ R/fl R/ft R/iX R/iY R/idx R/lh R/llx R/lly R/lp R/nH R/nSq R/newdict R/ps R/rad R/rev R/sL R/sba R/sbl R/sbs R/sn R/spa R/tB R/typ R/urx R/ury R/w R/wF R/xX R/xY R/rBg R/gBg R/bBg R/gry R/rDst R/gDst R/bDst R/cpd R/sf 20 d/cW 20 d/lW 20 d/bW 75 d/wF 1.5 d/aF 11.875 d/aR 0.263 d/aA 50 d/hS 54 d/pA 32 d/sh F d/S{sf m}b/dL{[hS] 0 setdash}b/o{1 ix}b/rot{3 -1 r}b/x{e d}b/CMT mt d/TM mt d/SM{CMT sm}b/XY{X D m Y D m a sq}b/s1 1 string d/fp{T charpath flattenpath}b/p{tr ru 0.25 a e ru 0.25 a e itransform}b/C{65536. dv rot 65536. dv rot 65536. dv rot setrgbcolor}b/sg{D currenthsbcolor P rot sethsbcolor currenthsbcolor e P e P o s D m .001 gt{setgray}{P}ie}b/sBg{65535 dv/bBg x 65535 dv/gBg x 65535 dv/rBg x}b/sRmp{currentrgbcolor bBg e s/bDst x gBg e s/gDst x rBg e s/rDst x}b/N 0 d/db{array/bs x/N 0 d}b/B{bs N rot put/N N 1 a d}b/SpA{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P 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whf}{Asc LB blf}{Asc LB gs f gr gs SM st gr np -1 -1 sc LB whf}{Ac whf}{OrA gAc}{Ac blf}{Ov whf}{OrA 1 .4 sc gOv}{Ov blf}}e 39 s g xc gr}ie}b/DS{np p M p l st}b/DD{gs dL DS gr}b/DB{gs 12 OB bW sl np 0 0 p M 0 p l st gr}b/ap{e 3 ix a e 2 ix a}b/PT{D 2 4 gi al P OP D 1 sc o length 6 gt{P 6 g}{e P 8 dv}ie D lW 2 m lt{P lW 2 m}if 0 e p 0 0 p 3 -1 r s 3 1 r e s e 0 0 p M 1 0 p l 0 0 p ap M 1 0 p ap l e n e n 0 0 p ap M 1 0 p ap l P P}b/DT{gs np PT SM st gr}b O/NH{lW s D hS dv ru cvi D 0 eq{P 1}if/nH x D hS nH m s D 0 lt{P .1 s nH dv}{nH 2 a dv D 0 xl 2 m s nH dv}ie}b/Bd{D type/arraytype ne{bs e g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b " q~~" q~~q*!FF=<F!)+!";")"h q|hvhh|v~vh"}v q|v~v|vP{""}P}" end %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 231 28 188 119 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 4423 2708 M 4413 2690 l 4694 2528 l 4694 2552 l cp f np 4972 2688 M 4962 2706 l 4694 2552 l 4694 2528 l cp f 6510 2640 5770 2640 73 Ar np 7203 2668 M 7193 2650 l 7474 2488 l 7474 2512 l cp f np 7752 2648 M 7742 2666 l 7474 2512 l 7474 2488 l cp f 4300 2540 4300 2740 66 Ar 5330 2580 5330 2780 67 Ar gr count origstk sub{P}rp end chemsave restore ,Times .+ǎH *+ 3 (N)&CO ++2 (RH *+ 2 (_N)&CO ++2 (H(f.dCHMDSTRGw  x (P6I Px PB  C   `x y <   z{| H3N H2NCO2HCO2 `  GR x T `  #T Ph , `  lc Pd ,  `  f x T,     Pf.Times' swsD Timesx! ED! ED& Timesx%! ED Timesx%CO2<! ED! E*D! ED@ ' '(( '! ED" 34CO26= ' ' ( J(8! EiD@! E^D& Timesx%! EuD Timesx%CO2H<  ! EuD! ED@! EiD! E^D '(( ' ' '! EuD" 34CO2H6= ' ' l`\  P  Pf.ļĤĜ     @-D'0 S&WordMicrosoft Word&Word V,  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. ,V CHMDGrphbjdCHMDacids and bases_str2dCHMD ,, ` #),, `,-^&'count   currentpoint 192837465 ! currentpoint  " save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform 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0 lt{-1 1 sc neg}if/X x np{{Y 16 div D 2 S lt{P 2 S}if/lp x lp 0 p M 0 0 p l 0 Y p l lp Y p l X lp s 0 p M X 0 p l X Y p l X lp s Y p l SM st}{Y 16 div D 2 S lt{P 2 S}if/lp x lp 0 p M 0 0 0 Y lp ac 0 Y 2 dv lp neg o lp ac 0 Y 2 dv 0 Y lp ac 0 Y lp Y lp ac X lp s 0 p M X 0 X Y lp ac X Y 2 dv X lp a o lp ac X Y 2 dv X Y lp ac X Y X lp s Y lp ac SM st}{Y D 2 dv Y 180 pA s 180 pA a arc st np X Y s Y 2 dv Y pA D neg arcn st}{Rc SM st}{X lW 2 dv a lW -2 dv p M rO D rlineto X lW 2 dv a rO a Y lW 2 dv a rO a p l rO lW -2 dv a Y lW 2 dv a rO a p l lW -2 dv Y lW 2 dv a p l 0 Y p l X Y p l X 0 p l cp f 0 0 p M 0 Y p l X Y p l X 0 p l cp SM st}{Rr SM st}{rO Y p M rO rO xl 0 Y X Y rO ac X Y X 0 rO ac X 0 0 0 rO ac rO neg D xl X Y 0 Y rO ac cp f Rr st}{Ac st}{OrA gAc}{Ov st}{OrA 1 .4 sc gOv}{Asc LB whf}{Asc gLB}{Asc gs gLB gr -1 -1 sc LB whf}{Asc gs gLB gr -0.4 -0.4 sc LB whf}{Asc LB gs whf gr np -0.4 -0.4 sc gLB}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro gs gDLB gr -1 -1 sc gDLB}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc gOv gr ZLB whf}{Asc gs -1 -1 sc gZLB gr gs 3.6 12 sc Cr whf gr gZLB}{0 0 p M X Y p l SM st}{bW sl 0 0 p M X Y p l SM st}{dL 0 0 p M X Y p l SM st}{OrA 1 16 dv D sc 0 -1 p M 0 0 1 0 1 ac 8 0 8 1 1 ac 8 0 16 0 1 ac 16 0 16 -1 1 ac SM st}{XY D 0 0 dt X Y dt}{XY 2 dv X Y dt}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{XY D X Y dt 0 0 M SM cpt xl 2 dv D sc 1 0 M -1 0 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l 2 0 M 0 0 2 0 360 arc Ast}{4.5 Aos 1 0 M -1 0 l 2 0 M 0 0 2 0 360 arc Ast}{2.25 Ath}{1.5 Ath}{1 Ath}{2.25 Aeq}{1.5 Aeq}{1 Aeq}{OrA 1 16 dv D sc 0 -1 p M 0 0 p l 16 0 p l 16 -1 p l SM st}{5 Aos 1 -1 M -1 -1 l 0 2 M 0 -2 l Ast}{5 Aos 1 -1 M -1 -1 l 1 1 M -1 1 l 0 2 M 0 -2 l Ast}{4.5 Aos 1 0 M -1 0 l 0 1 M 0 -1 l Ast}{4.5 Aos 1 0 M -1 0 l Ast}{gRc}{gRr}{Rc blf}{Rr blf}{Ac blf}{Ov blf}{Asc DLB -1 -1 sc DLB gs whf gr np 90 ro DLB -1 -1 sc DLB blf}{Asc gs -1 -1 sc ZLB blf gr gs 3.6 12 sc Cr whf gr ZLB blf}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc Cr blf gr ZLB whf}{Asc LB gs whf gr np -0.4 -0.4 sc LB blf}{Asc LB gs f gr gs SM st gr np -0.4 -0.4 sc LB whf}{Asc LB blf}{Asc LB gs f gr gs SM st gr np -1 -1 sc LB whf}{Ac whf}{OrA gAc}{Ac blf}{Ov whf}{OrA 1 .4 sc gOv}{Ov blf}}e 39 s g xc gr}ie}b/DS{np p M p l st}b/DD{gs dL DS gr}b/DB{gs 12 OB bW sl np 0 0 p M 0 p l st gr}b/ap{e 3 ix a e 2 ix a}b/PT{D 2 4 gi al P OP D 1 sc o length 6 gt{P 6 g}{e P 8 dv}ie D lW 2 m lt{P lW 2 m}if 0 e p 0 0 p 3 -1 r s 3 1 r e s e 0 0 p M 1 0 p l 0 0 p ap M 1 0 p ap l e n e n 0 0 p ap M 1 0 p ap l P P}b/DT{gs np PT SM st gr}b O/NH{lW s D hS dv ru cvi D 0 eq{P 1}if/nH x D hS nH m s D 0 lt{P .1 s nH dv}{nH 2 a dv D 0 xl 2 m s nH dv}ie}b/Bd{D type/arraytype ne{bs e g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b "<"Q"vQ"u<"<"Q"Q"<"Q"Q"<"Q"Q"<"Q"Q"g"g"g"|"|"|"""""""""""""""""""""")")")"?"?"?"T"Tend %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 376 140 56 369 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 1210 7882 M 1200 7892 l 1190 7892 l 1190 7450 l 1210 7470 l cp f np 1622 7882 M 1632 7892 l 1622 7902 l 1210 7902 l 1200 7892 l 1210 7882 l cp f np 1622 7470 M 1632 7460 l 1642 7470 l 1642 7882 l 1632 7892 l 1622 7882 l cp f np 1632 7450 M 1632 7460 l 1622 7470 l 1210 7470 l 1190 7450 l cp f np 1210 8314 M 1200 8324 l 1190 8324 l 1190 7892 l 1200 7892 l 1210 7902 l cp f np 1622 8314 M 1632 8324 l 1622 8334 l 1210 8334 l 1200 8324 l 1210 8314 l cp f np 1642 8314 M 1632 8324 l 1622 8314 l 1622 7902 l 1632 7892 l 1642 7902 l cp f np 1210 8746 M 1200 8756 l 1190 8756 l 1190 8324 l 1200 8324 l 1210 8334 l cp f np 1622 8746 M 1632 8756 l 1622 8766 l 1210 8766 l 1200 8756 l 1210 8746 l cp f np 1642 8746 M 1632 8756 l 1622 8746 l 1622 8334 l 1632 8324 l 1642 8334 l cp f np 1210 9178 M 1200 9188 l 1190 9188 l 1190 8756 l 1200 8756 l 1210 8766 l cp f np 1622 9178 M 1632 9188 l 1622 9198 l 1210 9198 l 1200 9188 l 1210 9178 l cp f np 1642 9178 M 1632 9188 l 1622 9178 l 1622 8766 l 1632 8756 l 1642 8766 l cp f np 1210 9610 M 1190 9630 l 1190 9188 l 1200 9188 l 1210 9198 l cp f np 1622 9610 M 1632 9620 l 1632 9630 l 1190 9630 l 1210 9610 l cp f np 1642 9610 M 1632 9620 l 1622 9610 l 1622 9198 l 1632 9188 l 1642 9198 l cp f np 2054 9610 M 2064 9620 l 2064 9630 l 1632 9630 l 1632 9620 l 1642 9610 l cp f np 2054 9198 M 2064 9188 l 2074 9198 l 2074 9610 l 2064 9620 l 2054 9610 l cp f np 2054 9178 M 2064 9188 l 2054 9198 l 1642 9198 l 1632 9188 l 1642 9178 l cp f np 2486 9610 M 2496 9620 l 2496 9630 l 2064 9630 l 2064 9620 l 2074 9610 l cp f np 2486 9198 M 2496 9188 l 2506 9198 l 2506 9610 l 2496 9620 l 2486 9610 l cp f np 2486 9178 M 2496 9188 l 2486 9198 l 2074 9198 l 2064 9188 l 2074 9178 l cp f np 2918 9610 M 2928 9620 l 2928 9630 l 2496 9630 l 2496 9620 l 2506 9610 l cp f np 2918 9198 M 2928 9188 l 2938 9198 l 2938 9610 l 2928 9620 l 2918 9610 l cp f np 2918 9178 M 2928 9188 l 2918 9198 l 2506 9198 l 2496 9188 l 2506 9178 l cp f np 3350 9610 M 3360 9620 l 3360 9630 l 2928 9630 l 2928 9620 l 2938 9610 l cp f np 3350 9198 M 3360 9188 l 3370 9198 l 3370 9610 l 3360 9620 l 3350 9610 l cp f np 3350 9178 M 3360 9188 l 3350 9198 l 2938 9198 l 2928 9188 l 2938 9178 l cp f np 3782 9610 M 3792 9620 l 3792 9630 l 3360 9630 l 3360 9620 l 3370 9610 l cp f np 3782 9198 M 3792 9188 l 3802 9198 l 3802 9610 l 3792 9620 l 3782 9610 l cp f np 3782 9178 M 3792 9188 l 3782 9198 l 3370 9198 l 3360 9188 l 3370 9178 l cp f np 4214 9610 M 4224 9620 l 4224 9630 l 3792 9630 l 3792 9620 l 3802 9610 l cp f np 4214 9198 M 4224 9188 l 4234 9198 l 4234 9610 l 4224 9620 l 4214 9610 l cp f np 4214 9178 M 4224 9188 l 4214 9198 l 3802 9198 l 3792 9188 l 3802 9178 l cp f np 4646 9610 M 4656 9620 l 4656 9630 l 4224 9630 l 4224 9620 l 4234 9610 l cp f np 4646 9198 M 4656 9188 l 4666 9198 l 4666 9610 l 4656 9620 l 4646 9610 l cp f np 4646 9178 M 4656 9188 l 4646 9198 l 4234 9198 l 4224 9188 l 4234 9178 l cp f np 5078 9610 M 5088 9620 l 5088 9630 l 4656 9630 l 4656 9620 l 4666 9610 l cp f np 5078 9198 M 5088 9188 l 5098 9198 l 5098 9610 l 5088 9620 l 5078 9610 l cp f np 5078 9178 M 5088 9188 l 5078 9198 l 4666 9198 l 4656 9188 l 4666 9178 l cp f np 5510 9610 M 5520 9620 l 5520 9630 l 5088 9630 l 5088 9620 l 5098 9610 l cp f np 5510 9198 M 5520 9188 l 5530 9198 l 5530 9610 l 5520 9620 l 5510 9610 l cp f np 5510 9178 M 5520 9188 l 5510 9198 l 5098 9198 l 5088 9188 l 5098 9178 l cp f np 5942 9610 M 5952 9620 l 5952 9630 l 5520 9630 l 5520 9620 l 5530 9610 l cp f np 5942 9198 M 5952 9188 l 5962 9198 l 5962 9610 l 5952 9620 l 5942 9610 l cp f np 5942 9178 M 5952 9188 l 5942 9198 l 5530 9198 l 5520 9188 l 5530 9178 l cp f np 6374 9610 M 6384 9620 l 6384 9630 l 5952 9630 l 5952 9620 l 5962 9610 l cp f np 6374 9198 M 6384 9188 l 6394 9198 l 6394 9610 l 6384 9620 l 6374 9610 l cp f np 6374 9178 M 6384 9188 l 6374 9198 l 5962 9198 l 5952 9188 l 5962 9178 l cp f np 6806 9610 M 6816 9620 l 6816 9630 l 6384 9630 l 6384 9620 l 6394 9610 l cp f np "T"j"j"j"""""""""""""""""""u"u"v"T"@"?"T"@"?"T"@"?"vT"u?"?"j"vj"uj""v"uj""u"j"j""""j"j6806 9198 M 6816 9188 l 6826 9198 l 6826 9610 l 6816 9620 l 6806 9610 l cp f np 6806 9178 M 6816 9188 l 6806 9198 l 6394 9198 l 6384 9188 l 6394 9178 l cp f np 7238 9610 M 7248 9620 l 7248 9630 l 6816 9630 l 6816 9620 l 6826 9610 l cp f np 7238 9198 M 7248 9188 l 7258 9198 l 7258 9610 l 7248 9620 l 7238 9610 l cp f np 7238 9178 M 7248 9188 l 7238 9198 l 6826 9198 l 6816 9188 l 6826 9178 l cp f np 7670 9610 M 7680 9620 l 7680 9630 l 7248 9630 l 7248 9620 l 7258 9610 l cp f np 7670 9198 M 7680 9188 l 7690 9198 l 7690 9610 l 7680 9620 l 7670 9610 l cp f np 7670 9178 M 7680 9188 l 7670 9198 l 7258 9198 l 7248 9188 l 7258 9178 l cp f np 8102 9610 M 8112 9620 l 8112 9630 l 7680 9630 l 7680 9620 l 7690 9610 l cp f np 8102 9198 M 8112 9188 l 8122 9198 l 8122 9610 l 8112 9620 l 8102 9610 l cp f np 8102 9178 M 8112 9188 l 8102 9198 l 7690 9198 l 7680 9188 l 7690 9178 l cp f np 8534 9610 M 8554 9630 l 8112 9630 l 8112 9620 l 8122 9610 l cp f np 8534 9198 M 8544 9188 l 8554 9188 l 8554 9630 l 8534 9610 l cp f np 8534 9178 M 8544 9188 l 8534 9198 l 8122 9198 l 8112 9188 l 8122 9178 l cp f np 8534 8766 M 8544 8756 l 8554 8756 l 8554 9188 l 8544 9188 l 8534 9178 l cp f np 8122 8766 M 8112 8756 l 8122 8746 l 8534 8746 l 8544 8756 l 8534 8766 l cp f np 8102 8766 M 8112 8756 l 8122 8766 l 8122 9178 l 8112 9188 l 8102 9178 l cp f np 8534 8334 M 8544 8324 l 8554 8324 l 8554 8756 l 8544 8756 l 8534 8746 l cp f np 8122 8334 M 8112 8324 l 8122 8314 l 8534 8314 l 8544 8324 l 8534 8334 l cp f np 8102 8334 M 8112 8324 l 8122 8334 l 8122 8746 l 8112 8756 l 8102 8746 l cp f np 8534 7902 M 8544 7892 l 8554 7892 l 8554 8324 l 8544 8324 l 8534 8314 l cp f np 8122 7902 M 8112 7892 l 8122 7882 l 8534 7882 l 8544 7892 l 8534 7902 l cp f np 8102 7902 M 8112 7892 l 8122 7902 l 8122 8314 l 8112 8324 l 8102 8314 l cp f np 8534 7470 M 8554 7450 l 8554 7892 l 8544 7892 l 8534 7882 l cp f np 8122 7470 M 8112 7460 l 8112 7450 l 8554 7450 l 8534 7470 l cp f np 8102 7470 M 8112 7460 l 8122 7470 l 8122 7882 l 8112 7892 l 8102 7882 l cp f np 6806 8766 M 6816 8756 l 6826 8766 l 6826 9178 l 6816 9188 l 6806 9178 l cp f np 6394 8766 M 6384 8756 l 6394 8746 l 6806 8746 l 6816 8756 l 6806 8766 l cp f np 6374 8766 M 6384 8756 l 6394 8766 l 6394 9178 l 6384 9188 l 6374 9178 l cp f np 6806 8334 M 6816 8324 l 6826 8334 l 6826 8746 l 6816 8756 l 6806 8746 l cp f np 6394 8334 M 6384 8324 l 6394 8314 l 6806 8314 l 6816 8324 l 6806 8334 l cp f np 6374 8334 M 6384 8324 l 6394 8334 l 6394 8746 l 6384 8756 l 6374 8746 l cp f np 6806 7902 M 6816 7892 l 6826 7902 l 6826 8314 l 6816 8324 l 6806 8314 l cp f np 6394 7902 M 6384 7892 l 6394 7882 l 6806 7882 l 6816 7892 l 6806 7902 l cp f np 6374 7892 M 6384 7892 l 6394 7902 l 6394 8314 l 6384 8324 l 6374 8314 l cp f np 6806 7470 M 6816 7460 l 6826 7470 l 6826 7882 l 6816 7892 l 6806 7882 l cp f np 6394 7470 M 6374 7450 l 6816 7450 l 6816 7460 l 6806 7470 l cp f np 6374 7450 M 6394 7470 l 6394 7882 l 6384 7892 l 6374 7892 l cp f np 7238 7882 M 7248 7892 l 7238 7902 l 6826 7902 l 6816 7892 l 6826 7882 l cp f np 7238 7470 M 7248 7460 l 7258 7470 l 7258 7882 l 7248 7892 l 7238 7882 l cp f np 7248 7450 M 7248 7460 l 7238 7470 l 6826 7470 l 6816 7460 l 6816 7450 l cp f np 7670 7882 M 7680 7892 l 7670 7902 l 7258 7902 l 7248 7892 l 7258 7882 l cp f np 7670 7470 M 7680 7460 l 7690 7470 l 7690 7882 l 7680 7892 l 7670 7882 l cp f np 7680 7450 M 7680 7460 l 7670 7470 l 7258 7470 l 7248 7460 l 7248 7450 l cp f np 7690 7902 M 7680 7892 l 7690 7882 l 8102 7882 l 8112 7892 l 8102 7902 l cp f np 7690 7470 M 7680 7460 l 7680 7450 l 8112 7450 l 8112 7460 l 8102 7470 l cp f np 7238 8314 M 7248 8324 l 7238 8334 l 6826 8334 l 6816 8324 l 6826 8314 l cp f np 7258 8314 M 7248 8324 l 7238 8314 l 7238 7902 l 7248 7892 l 7258 7902 l cp f np 7670 8314 M 7680 8324 l 7670 8334 l 7258 8334 l 7248 8324 l 7258 8314 l cp f np 7690 8314 M 7680 8324 l 7670 8314 l 7670 7902 l 7680 7892 l 7690 7902 l cp f np 7690 8334 M 7680 8324 l 7690 8314 l 8102 8314 l 8112 8324 l 8102 8334 l cp f np 7238 8746 M 7248 8756 l 7238 8766 l 6826 8766 l 6816 8756 l 6826 8746 l cp f np 7258 """"j""R"g"R"g"|"|"h"|"g"g"ug"uR"""""""""""""""""""""")")""*"*"""""""")8746 M 7248 8756 l 7238 8746 l 7238 8334 l 7248 8324 l 7258 8334 l cp f np 7670 8746 M 7680 8756 l 7670 8766 l 7258 8766 l 7248 8756 l 7258 8746 l cp f np 7690 8746 M 7680 8756 l 7670 8746 l 7670 8334 l 7680 8324 l 7690 8334 l cp f np 7690 8766 M 7680 8756 l 7690 8746 l 8102 8746 l 8112 8756 l 8102 8766 l cp f np 7238 8766 M 7248 8756 l 7258 8766 l 7258 9178 l 7248 9188 l 7238 9178 l cp f np 7670 8766 M 7680 8756 l 7690 8766 l 7690 9178 l 7680 9188 l 7670 9178 l cp f np 1642 8766 M 1632 8756 l 1642 8746 l 2054 8746 l 2064 8756 l 2054 8766 l cp f np 2054 8334 M 2064 8324 l 2074 8334 l 2074 8746 l 2064 8756 l 2054 8746 l cp f np 1642 8334 M 1632 8324 l 1642 8314 l 2054 8314 l 2064 8324 l 2054 8334 l cp f np 2074 9178 M 2064 9188 l 2054 9178 l 2054 8766 l 2064 8756 l 2074 8766 l cp f np 2486 8746 M 2496 8756 l 2486 8766 l 2074 8766 l 2064 8756 l 2074 8746 l cp f np 2486 8334 M 2496 8324 l 2506 8334 l 2506 8746 l 2496 8756 l 2486 8746 l cp f np 2496 8314 M 2496 8324 l 2486 8334 l 2074 8334 l 2064 8324 l 2074 8314 l cp f np 2486 8766 M 2496 8756 l 2506 8766 l 2506 9178 l 2496 9188 l 2486 9178 l cp f np 2054 7902 M 2064 7892 l 2074 7892 l 2074 8314 l 2064 8324 l 2054 8314 l cp f np 2054 7882 M 2064 7892 l 2054 7902 l 1642 7902 l 1632 7892 l 1642 7882 l cp f np 2054 7470 M 2074 7450 l 2074 7892 l 2064 7892 l 2054 7882 l cp f np 2074 7450 M 2054 7470 l 1642 7470 l 1632 7460 l 1632 7450 l cp f np 2918 8746 M 2928 8756 l 2918 8766 l 2506 8766 l 2496 8756 l 2506 8746 l cp f np 2918 8334 M 2928 8324 l 2938 8334 l 2938 8746 l 2928 8756 l 2918 8746 l cp f np 2928 8314 M 2928 8324 l 2918 8334 l 2506 8334 l 2496 8324 l 2496 8314 l cp f np 3350 8746 M 3360 8756 l 3350 8766 l 2938 8766 l 2928 8756 l 2938 8746 l cp f np 3350 8334 M 3360 8324 l 3370 8334 l 3370 8746 l 3360 8756 l 3350 8746 l cp f np 3360 8314 M 3360 8324 l 3350 8334 l 2938 8334 l 2928 8324 l 2928 8314 l cp f np 3782 8746 M 3792 8756 l 3782 8766 l 3370 8766 l 3360 8756 l 3370 8746 l cp f np 3782 8334 M 3792 8324 l 3802 8334 l 3802 8746 l 3792 8756 l 3782 8746 l cp f np 3792 8314 M 3792 8324 l 3782 8334 l 3370 8334 l 3360 8324 l 3360 8314 l cp f np 4214 8746 M 4224 8756 l 4214 8766 l 3802 8766 l 3792 8756 l 3802 8746 l cp f np 4214 8334 M 4224 8324 l 4234 8334 l 4234 8746 l 4224 8756 l 4214 8746 l cp f np 4224 8314 M 4224 8324 l 4214 8334 l 3802 8334 l 3792 8324 l 3792 8314 l cp f np 4646 8746 M 4656 8756 l 4646 8766 l 4234 8766 l 4224 8756 l 4234 8746 l cp f np 4646 8334 M 4656 8324 l 4666 8334 l 4666 8746 l 4656 8756 l 4646 8746 l cp f np 4656 8314 M 4656 8324 l 4646 8334 l 4234 8334 l 4224 8324 l 4224 8314 l cp f np 5078 8746 M 5088 8756 l 5078 8766 l 4666 8766 l 4656 8756 l 4666 8746 l cp f np 5078 8334 M 5088 8324 l 5098 8334 l 5098 8746 l 5088 8756 l 5078 8746 l cp f np 5088 8314 M 5088 8324 l 5078 8334 l 4666 8334 l 4656 8324 l 4656 8314 l cp f np 5510 8746 M 5520 8756 l 5510 8766 l 5098 8766 l 5088 8756 l 5098 8746 l cp f np 5510 8334 M 5520 8324 l 5530 8334 l 5530 8746 l 5520 8756 l 5510 8746 l cp f np 5520 8314 M 5520 8324 l 5510 8334 l 5098 8334 l 5088 8324 l 5088 8314 l cp f np 5942 8746 M 5952 8756 l 5942 8766 l 5530 8766 l 5520 8756 l 5530 8746 l cp f np 5942 8334 M 5952 8324 l 5962 8334 l 5962 8746 l 5952 8756 l 5942 8746 l cp f np 5952 8314 M 5952 8324 l 5942 8334 l 5530 8334 l 5520 8324 l 5520 8314 l cp f np 5962 8766 M 5952 8756 l 5962 8746 l 6374 8746 l 6384 8756 l 6374 8766 l cp f np 5962 8334 M 5952 8324 l 5952 8314 l 6374 8314 l 6384 8324 l 6374 8334 l cp f np 2918 8766 M 2928 8756 l 2938 8766 l 2938 9178 l 2928 9188 l 2918 9178 l cp f np 3350 8766 M 3360 8756 l 3370 8766 l 3370 9178 l 3360 9188 l 3350 9178 l cp f np 3782 8766 M 3792 8756 l 3802 8766 l 3802 9178 l 3792 9188 l 3782 9178 l cp f np 4214 8766 M 4224 8756 l 4234 8766 l 4234 9178 l 4224 9188 l 4214 9178 l cp f np 4646 8766 M 4656 8756 l 4666 8766 l 4666 9178 l 4656 9188 l 4646 9178 l cp f np 5078 8766 M 5088 8756 l 5098 8766 l 5098 9178 l 5088 9188 l 5078 9178 l cp f np 5510 8766 M 5520 8756 l 5530 8766 l 5530 9178 l 5520 9188 l 5510 9178 l cp f np 5942 8766 M 5952 8756 l 5962 8766 l 5962 "#O##"#O##"###"###"!J##"!H##9178 l 5952 9188 l 5942 9178 l cp f 8320 9540 8320 7840 11 Ar 6480 7720 8200 7720 11 Ar 1355 9427 8230 7839 11 Ar gr count origstk sub{P}rp end chemsave restore ,Times .(F(e:Electronegativity decreases as we move away from fluorine.dCHMDSTRGq8  x (P6 %D   (P(  $K &$`$`"4@ A  `"4"4`##`%%`%#% # % p# p% # %#%#%0#0%#%#%@#@%#%#%P#P%#%#%!`#!`"4!`"4 !` !`$!` $ "4"4  $$ P$$P%)$* P0 3"4P7"4:"4 F GL$O"4 pR pS"4 W X"4\ ]"4a b"40f 0g"4k l"4p q"4@u @v BCD            !! ""#!#"$$%#%$&&'%'&(()')(**+)+*,,-+--../+/.001/10223 13 24 4535%667#76889798::;9;:<!<=";=#:>&>?'<?(>@+@A,?A-3@.5A/8B1>B2BC4@C51C66D8BD9DE;CE</E='D>)E?EFHFGIGJFKHMHNHIPIQFJTJKUGKVJLYLMZKM[LN^NO_MO`NPcPQdOQePRhRSiQSjRTmTUnSUoTVrVWsUWtVXwXYxWYy7Xz9Y{J|L}N~PRTV!X  d X Xd F:  '`&'x:Electronegativity decreases as we move away from fluorine.Times'4swsD Timesd! DEi ! DEv! DMEv! DMEi  ' ' ' '! DE! DME ' '  ' ! DE! DME '  '  ' ! DEp! DMEp '  ' '! DEP! DMEP ' ' '! DEP! DEp ' ' '! D@EP! D@Ep '! '!" '"! DEP! DEp '!& '&' '"'! DEP! DEp '&+ '+, '',! DEP! DEp '+0 '01 ',1! EEP! EEp '05 '56 '16! EEP! EEp '5: ':; '6;! EEP! EEp ':? '?@ ';@! E,EP! E,Ep '?D 'DE '@E! E:@EP! E:@Ep 'DI 'IJ 'EJ! EG`EP! EG`Ep 'IN 'NO 'JO! EU EP! EU Ep 'NS 'ST 'OT! Eb@EP! Eb@Ep 'SX 'XY 'TY! EpEP! EpEp 'X] ']^ 'Y^! E}EP! E}Ep ']b 'bc '^c! EpEP! EpEp 'bg 'gh 'ch! EpE! E}E 'hl 'lm 'cm! EpE! E}E 'lq 'qr 'mr! EpEv! E}Ev 'qv 'vw 'rw! EpEi ! E}Ei  'v{ '{| 'w|! EU E! EG`E 'T ' 'O! EU E! EG`E ' ' '! EU Ev! EG`Ev ' ' '! EU Ei ! EG`Ei  ' ' '! Eb@Ev! Eb@Ei  ' ' '! EpEv! EpEi  ' ' ' 'w '|! Eb@E ' '! EpE ' ' 'r! Eb@E ' '! EpE ' ' 'm 'Y '^! DE! DE ' ' '  '! D@E! D@E ' ' ' '"! DEv ' '! DEi  ' '! DE! DE ' ' '! DE! DE ' ' '! DE! DE ' ' '! EE! EE ' ' '! EE! EE ' ' '! EE! EE ' ' '! E,E! E,E ' ' '! E:@E! E:@E ' ' ' ' ' '' ', '1 '6 '; '@ 'E 'J ,[W Xd  Xd FļĤĜ    @ @@P8 8 `<xt&'x&'x:Electronegativity decreases as we move away from fluorine.ļĤĜ                                                             @ fP82D N4$ S&WordMicrosoft Word&Word 0  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. 01M 1MCHMD1MGrphbjdCHMDacids and bases_str2dCHMD ,, ` #),, `,-^&'count  /0 1Mcurrentpoint 192837465 !1 currentpoint  1M"1 save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform L/xl/translate L/xc/exec L/A R/N R/St R/X R/Y R/aL R/bL R/bS R/bd R/bs R/cX R/cY R/ch R/co R/fB R/fI R/fS R/fZ R/fl R/ft R/iX R/iY R/idx R/lh R/llx R/lly R/lp R/nH R/nSq R/newdict R/ps R/rad R/rev R/sL R/sba R/sbl R/sbs R/sn R/spa R/tB R/typ R/urx R/ury R/w R/wF R/xX R/xY R/rBg R/gBg R/bBg R/gry R/rDst R/gDst R/bDst R/cpd R/sf 20 d/cW 20 d/lW 20 d/bW 75 d/wF 1.5 d/aF 11.875 d/aR 0.263 d/aA 50 d/hS 54 d/pA 32 d/sh F d/S{sf m}b/dL{[hS] 0 setdash}b/o{1 ix}b/rot{3 -1 r}b/x{e d}b/CMT mt d/TM mt d/SM{CMT sm}b/XY{X D m Y D m a sq}b/s1 1 string d/fp{T charpath flattenpath}b/p{tr ru 0.25 a e ru 0.25 a e itransform}b/C{65536. dv rot 65536. dv rot 65536. dv rot setrgbcolor}b/sg{D currenthsbcolor P rot sethsbcolor currenthsbcolor e P e P o s D m .001 gt{setgray}{P}ie}b/sBg{65535 dv/bBg x 65535 dv/gBg x 65535 dv/rBg x}b/sRmp{currentrgbcolor bBg e s/bDst x gBg e s/gDst x rBg e s/rDst x}b/N 0 d/db{array/bs x/N 0 d}b/B{bs N rot put/N N 1 a d}b/SpA{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie aR aL m n D aL a 0 p M 0 o n aA n aA arc cp f gr}b/SpH{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie 0 cw 2 dv xl aR aL m n D aL a 0 p M 0 o n aA n 0 arc cp f gr}b/Sp{/St x 0.316/aR x gs aF lW m 0.8 m St 4 and 0 ne{bW m lW dv bW sl}if/aL x St 8 and 0 ne{8 ix 8 ix 3 ix 3 ix SpA}if St 16 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpA}if St 32 and 0 ne{8 ix 8 ix 3 ix 3 ix SpH}if St 64 and 0 ne{2 ix 6 m 1 a D ix e D ix e D ix e D ix e P SpH}if St 2 and 0 ne{St 4 and 0 ne{[hS bW m lW dv] 0 setdash}{dL}ie}if np M{cv}rp St 128 and 0 ne{f}{st}ie gr}b/Ha{gs np 3 1 r xl D sc -.7 1.4 p M 0.7 1.4 p l -.7 2.4 p M 0.7 2.4 p l SM st gr}b/OP{3 ix 3 ix xl 3 -1 r s 3 1 r e s o o at ro D m e D m a sq}b/OB{/bS x OP D bS dv D lW 2 m lt{P lW 2 m}if/bd x}b/DA{np 0 0 M aL 0 aR aL m 180 aA s 180 aA a arc cp f}b/OA{np 0 cw -2 dv M aL 0 aR aL m 180 aA s 180 arc 0 cw -2 dv rlineto cp f}b/Ast{SM cw 0.8 m sl st}b/SA{aF m lW m/aL x 0.263/aR x aL 1 aR s m np 0 p M rad 0 p l gs Ast gr}b/CA{aF lW m 0.8 m/aL x 0.316/aR x aL 1 aR s m 2 dv rad D m o D m s D 0 le{P P P}{sq at 2 m np rad 0 rad 180 6 -1 r s 180 6 -1 r s arc gs Ast gr cpt e at ro}ie}b/AA{np rad 0 rad 180 180 6 -1 r a arc gs SM st gr}b/RA{lW m/w x np rad w p M w .7 dv w p l rad w n p M w .7 dv w n p l w .35 dv w 2 m p M 0 0 p l w .35 dv w -2 m p l st}b/HA{lW m/w x np 0 0 p M w 2 m D p l w 2 m w p l rad w p l rad w n p l w 2 m w n p l w 2 m D n p l cp st}b/Ar1{gs 5 1 r OP/rad x{{2.25 SA DA}{1.5 SA DA}{1 SA DA}{lW 4 m sl 4.5 SA DA}{lW 4 m sl 3 SA DA}{lW 4 m sl 2 SA DA}{270 CA DA}{180 CA DA}{120 CA DA}{90 CA DA}{2.5 RA}{2.5 HA}{1 -1 sc 270 CA DA}{1 -1 sc 180 CA DA}{1 -1 sc 120 CA DA}{1 -1 sc 90 CA DA}{5 RA}{5 HA}{dL 2.25 SA DA}{dL 1.5 SA DA}{dL 1 SA DA}{2.25 SA OA}{1.5 SA OA}{1 SA OA}{1 -1 sc 2.25 SA OA}{1 -1 sc 1.5 SA OA}{1 -1 sc 1 SA 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o xl 3 -1 r e s 3 1 r s e o 0 lt o 0 lt ne/rev x D 0 lt{1 -1 sc neg}if/Y x D 0 lt{-1 1 sc neg}if/X x np{{Y 16 div D 2 S lt{P 2 S}if/lp x lp 0 p M 0 0 p l 0 Y p l lp Y p l X lp s 0 p M X 0 p l X Y p l X lp s Y p l SM st}{Y 16 div D 2 S lt{P 2 S}if/lp x lp 0 p M 0 0 0 Y lp ac 0 Y 2 dv lp neg o lp ac 0 Y 2 dv 0 Y lp ac 0 Y lp Y lp ac X lp s 0 p M X 0 X Y lp ac X Y 2 dv X lp a o lp ac X Y 2 dv X Y lp ac X Y X lp s Y lp ac SM st}{Y D 2 dv Y 180 pA s 180 pA a arc st np X Y s Y 2 dv Y pA D neg arcn st}{Rc SM st}{X lW 2 dv a lW -2 dv p M rO D rlineto X lW 2 dv a rO a Y lW 2 dv a rO a p l rO lW -2 dv a Y lW 2 dv a rO a p l lW -2 dv Y lW 2 dv a p l 0 Y p l X Y p l X 0 p l cp f 0 0 p M 0 Y p l X Y p l X 0 p l cp SM st}{Rr SM st}{rO Y p M rO rO xl 0 Y X Y rO ac X Y X 0 rO ac X 0 0 0 rO ac rO neg D xl X Y 0 Y rO ac cp f Rr st}{Ac st}{OrA gAc}{Ov st}{OrA 1 .4 sc gOv}{Asc LB whf}{Asc gLB}{Asc gs gLB gr -1 -1 sc LB whf}{Asc gs gLB gr -0.4 -0.4 sc LB whf}{Asc LB gs whf gr np -0.4 -0.4 sc gLB}{Asc DLB 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gr gs 3.6 12 sc Cr whf gr ZLB blf}{Asc gs -1 -1 sc ZLB whf gr gs 3.6 12 sc Cr blf gr ZLB whf}{Asc LB gs whf gr np -0.4 -0.4 sc LB blf}{Asc LB gs f gr gs SM st gr np -0.4 -0.4 sc LB whf}{Asc LB blf}{Asc LB gs f gr gs SM st gr np -1 -1 sc LB whf}{Ac whf}{OrA gAc}{Ac blf}{Ov whf}{OrA 1 .4 sc gOv}{Ov blf}}e 39 s g xc gr}ie}b/DS{np p M p l st}b/DD{gs dL DS gr}b/DB{gs 12 OB bW sl np 0 0 p M 0 p l st gr}b/ap{e 3 ix a e 2 ix a}b/PT{D 2 4 gi al P OP D 1 sc o length 6 gt{P 6 g}{e P 8 dv}ie D lW 2 m lt{P lW 2 m}if 0 e p 0 0 p 3 -1 r s 3 1 r e s e 0 0 p M 1 0 p l 0 0 p ap M 1 0 p ap l e n e n 0 0 p ap M 1 0 p ap l P P}b/DT{gs np PT SM st gr}b O/NH{lW s D hS dv ru cvi D 0 eq{P 1}if/nH x D hS nH m s D 0 lt{P .1 s nH dv}{nH 2 a dv D 0 xl 2 m s nH dv}ie}b/Bd{D type/arraytype ne{bs e g}if{{P}{{{DS}{DD}{gs 12 OB np bW 2 dv/bd x lW 2 dv e D NH e{D bd p M bd n p l}for st gr}{gs 12 OB np lW 2 dv 0 xl NH 1 sc bW 2 dv wF m nH 1 a dv/bd x 0 1 nH{D 1 a bd m o o p M n p l}for SM st gr}{P}{DB}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp f gr}{P}{gs 12 OB/bL x bW 2 dv D lW lt{P lW}if/bd x np 0 0 p M bL bd 4 m dv ru 2 o o lt{e}if P cvi/nSq x bL nSq 2 m dv D sc nSq{.135 .667 .865 .667 1 0 rcurveto .135 -.667 .865 -.667 1 0 rcurveto}rp SM st gr}{gs 12 OB np 0 lW 2 dv o o n p M p l bW 2 dv wF m o o p l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b QQQ7:Q7:Q Q Q69Q69QEHQEHQ'*Q"%Q@CQ;>Q@CQ;>P2;"6P4="8Q QQ*- Q*-QDG QDGQ58 Q58Q@ BQ; =Q& (Q! #Q@BQ;=P1:"5end %%EndProcSet 40 80 20 20 54 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 233 53 49 280 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C 3730 5710 3630 5710 62 Ar 3730 6250 3630 6250 62 Ar 4670 5730 4570 5730 62 Ar 4630 6230 4530 6230 62 Ar 4630 6530 4530 6530 62 Ar 4730 5930 4730 5830 62 Ar 3550 6430 3550 6330 62 Ar 4710 6430 4710 6330 62 Ar 3490 6190 3490 6390 67 Ar 4810 6230 4810 6430 67 Ar 5270 5710 5170 5710 62 Ar 5270 5990 5170 5990 62 Ar 5290 6510 5190 6510 62 Ar 5310 6210 5210 6210 62 Ar 5390 6418 5390 6318 62 Ar 5370 5898 5370 5798 62 Ar 5130 6418 5130 6318 62 Ar 5470 6170 5470 6370 67 Ar gr count origstk sub{P}rp end chemsave restore ,Times .()3 Acid: ))`CH Ԁ+4 T() NH + 3 )() H +2 T()O )  HF (C3Conjugate base: {)_CH &+3 (C NH + 2 {(C HO FdPCHMDSTRG1M  x (P6>dXX8>dtt8>dlHl>d` `>d >dXX<>dpp<>dxxP>dLLd>d>d4>d>d(  >d(pp>dC8  C`(C$hhi* ` 0D M`U 4x78i Acid: CH4 NH3 H2O HF Conjugate base: CH3 NH2 HO FTimes'swsD Timesx  J.c_xxi Acid: CH4 NH3 H2O HF Conjugate base: CH3 NH2 HO FļĤĜ                                                                                                            @DCD-  S&WordMicrosoft Word&Word A  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. A)%p %)pCHMD)%pGrphbjdCHMDacids and bases_str3dCHMD ,, ` #),, `,-^&'count  '#($ )%pcurrentpoint 192837465 !)% currentpoint  )%p"% save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill L/fa/forall L/g/get L/gi/getinterval L/gr/grestore L/gs/gsave L/ie/ifelse L/ix/index L/l/lineto L/mt/matrix L/M/moveto L/m/mul L/n/neg L/np/newpath L/pb/pathbbox L/P/pop L/r/roll L/rm/rmoveto L/ro/rotate L/rp/repeat L/ru/round L/sc/scale L/sl/setlinewidth L/sm/setmatrix L/st/stroke L/sp/strokepath L/sq/sqrt L/s/sub L/T/true L/tr/transform L/xl/translate L/xc/exec L/A R/N R/St R/X R/Y R/aL R/bL R/bS R/bd R/bs R/cX R/cY R/ch R/co R/fB R/fI R/fS R/fZ R/fl R/ft R/iX R/iY R/idx R/lh R/llx R/lly R/lp R/nH R/nSq R/newdict R/ps R/rad R/rev R/sL R/sba R/sbl R/sbs R/sn R/spa R/tB R/typ R/urx R/ury R/w R/wF R/xX R/xY R/rBg R/gBg R/bBg R/gry R/rDst R/gDst R/bDst R/cpd R/sf 20 d/cW 20 d/lW 20 d/bW 75 d/wF 1.5 d/aF 11.875 d/aR 0.263 d/aA 50 d/hS 54 d/pA 32 d/sh F d/S{sf m}b/dL{[hS] 0 setdash}b/o{1 ix}b/rot{3 -1 r}b/x{e d}b/CMT mt d/TM mt d/SM{CMT sm}b/XY{X D m Y D m a sq}b/s1 1 string d/fp{T charpath flattenpath}b/p{tr ru 0.25 a e ru 0.25 a e itransform}b/C{65536. dv rot 65536. dv rot 65536. dv rot setrgbcolor}b/sg{D currenthsbcolor P rot sethsbcolor currenthsbcolor e P e P o s D m .001 gt{setgray}{P}ie}b/sBg{65535 dv/bBg x 65535 dv/gBg x 65535 dv/rBg x}b/sRmp{currentrgbcolor bBg e s/bDst x gBg e s/gDst x rBg e s/rDst x}b/N 0 d/db{array/bs x/N 0 d}b/B{bs N rot put/N N 1 a d}b/SpA{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie aR aL m n D aL a 0 p M 0 o n aA n aA arc cp f gr}b/SpH{gs np o o xl rot s e rot s o 0 ne o 0 ne or{at ro}{P P}ie 0 cw 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l n p l cp SM lW 0.8 m sl st gr}{P}{4 2 r gs OP/rad x 1 SA DA gr}{P}}o 1 g 1 s g e 2 4 gi al P 5 -1 r xc}{al P 8 ix 1 eq{DD}{DS}ie 5 -1 r 2 eq{DB}{DS}ie P}{DT}}o 0 g g xc}b /SP{/sf x/lW x/bW x/cW x SPn}b/SPn{gs count 9 ge 7 ix 192837465 eq and{7 -1 r P 6 -2 r o o xl 7 -1 r s e 7 -1 r s e 5 -1 r dv neg e 5 -1 r dv neg e sc neg e neg e xl}{xl P P}ie 1 1 S dv D sc CMT currentmatrix P lW sl 4.0 setmiterlimit np}b ":# "jJ"jL"d"# "l"lq2u|'y'|yvy'yu y { y"x"/"N"M"o@Q3b6eQ3]6`QAdDgQA_DbQ}`bQ}[]Q`bQ[]Q25Q25Q?BQ?BQ~Q~QQQaBdEQa=d@QVYQZ]Q;>Q69QeDhGQ`DcGQeQhTQ`QcTQgjQbeQgjQbeQQQj9m<Qe9h<QjEmHQeEhHQMPQQTP-6"1Px"|P\GeP"`Iq8>;>;8;":qtzwzwtw"vend %%EndProcSet 40 80 20 20 29 chemdict30 begin/hS x/sf x/lW x/bW x/cW x/sh T d 331 123 37 41 SPn/origstk x 65535 65535 65535 sBg 0 0 0 C np 1176 2635 M 1166 2617 l 1510 2418 l 1510 2442 l cp f np 1775 2571 M 1765 2589 l 1510 2442 l 1510 2418 l cp f np 1474 2110 M 1494 2110 l 1494 2445 l 1474 2445 l cp f np 1526 2110 M 1546 2110 l 1546 2445 l 1526 2445 l cp f np 2015 2582 M 2005 2564 l 2125 2495 l 2135 2513 l cp f np 3976 2675 M 3966 2657 l 4310 2458 l 4310 2482 l cp f np 4575 2611 M 4565 2629 l 4310 2482 l 4310 2458 l cp f np 4274 2150 M 4294 2150 l 4294 2485 l 4274 2485 l cp f np 4326 2150 M 4346 2150 l 4346 2485 l 4326 2485 l cp f 5890 2410 5152 2410 70 Ar np 6076 2735 M 6066 2717 l 6400 2524 l 6420 2536 l cp f np 6686 2647 M 6676 2665 l 6405 2509 l 6415 2491 l cp f np 6660 2693 M 6650 2711 l 6379 2554 l 6389 2536 l cp f np 6400 2210 M 6420 2210 l 6420 2536 l 6400 2524 l cp f 1990 1050 1890 1050 62 Ar 2030 1330 1930 1330 62 Ar 1944 2530 1844 2530 62 Ar 1944 2790 1844 2790 62 Ar 4650 1030 4550 1030 62 Ar 4670 1290 4570 1290 62 Ar 4750 2550 4650 2550 62 Ar 4744 2830 4644 2830 62 Ar 6470 1970 6370 1970 62 Ar 6869 2643 6945 2707 62 Ar 4750 1210 4750 1110 62 Ar 1390 2050 1390 1950 62 Ar 1650 2050 1650 1950 62 Ar 4210 2090 4210 1990 62 Ar 4450 2090 4450 1990 62 Ar 4830 2750 4830 2650 62 Ar 6290 2150 6290 2050 62 Ar 6530 2150 6530 2050 62 Ar 6689 2823 6765 2887 62 Ar 4830 970 4830 1170 67 Ar 4897 2470 4897 2670 67 Ar 6610 1910 6610 2110 67 Ar 3510 1170 2610 1170 2 Ar 3510 2370 2610 2370 2 Ar gr count origstk sub{P}rp end chemsave restore ,Times .+&CH ++3 (ZO(hHO+%H+E CH ++3 (O(jO(@6CH ++3 (@KCH W+2 (@`OH(? CH ++3 (?CH W+2 (?O+6NCH ++3 (OO(m=O((Acetate ion: two contributing structures(REthoxide ion: no resonance(SBEthanol(: Acetic acid(7remove+proton(sremove+protondCHMDSTRG)%p  x (PF t t*>d$$l%>d<<&>d  >'>d  >(>d4)>dH*>d  4+>d  .,>dP->c ] +/>d`0>d xx1>d ||2>d4||3>d4ll4>d  d5>dp 6>dp 7>c + Qw8C;C + x+<CH=  <@ L L <C  `z   j `f  V  <       CH3H CH3OOO O CH3 O! O `     `   8 $ `   <  `     ` (,F `   <  ` PT6 `  ! x0 T `  :# x@  ` "j ` 8`8<CH3CH2OH ` `L(\ CH3CH2O(   l $ (Acetate ion: two contributing structures  h.hEthoxide ion: no resonance  |(9(| Ethanol   : T  Acetic acid U L x> xL 4remove   ?  proton U  xA x 4remove   < B x protonTimes'swsD$ Timesx! D>D! DD@& TimesxCH3^! DmD@ Timesx ' '! D>Dz Timesx '(! D@D Timesx '! ED! D@D& TimesxCH3^! ED Timesx '  ' ! ED Timesx ' ( 0 ~z`8<`8<CH3CH2OHļĤĜ  $         @ N& ~zL(\L(\ CH3CH2OļĤĜ  $         @  8! EHD! E<D& TimesxCH3^! ETD Timesx ' '(! EHD@ Timesx '   (Acetate ion: two contributing structuresļĤĜ                                           @ lhhEthoxide ion: no resonanceļĤĜ  l                           @ xyu(| (| EthanolļĤĜ          @ D|J T  T  Acetic acidļĤĜ  0            @ <btp xL 4 xL 4removeļĤĜ         @ PvRtp    protonļĤĜ         @ NN8 <Btp x 4 x 4removeļĤĜ         @ Ptp x x protonļĤĜ         @ 8@D/  S&WordMicrosoft Word&Word @?  2 @@$Use Word 6.0c or later to 2 @$view Macintosh picture. ?@,. ,.CHMD,.GrphbjdCHMDacids and bases_str3dCHMD ,, ` #),, `,-^&'count  *+ ,.currentpoint 192837465 !, currentpoint  ,.", save/chemsave exch def %%BeginProcSet: chemdict30 24 10 % ChemDraw Laser Prep % Copyright 1986-1995, CambridgeSoft Corporation userdict/chemdict30 210 dict put chemdict30 begin/version 24 def/sv 10 def/b{bind def}bind def/L{load def}b/R{null def}b/d/def L/a/add L/al/aload L/as/astore L/at/atan L/cp/closepath L/cv/curveto L/cw/currentlinewidth L/cpt/currentpoint L/dv/div L/D/dup L/e/exch L/F/false L/f/fill 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]>dj^>d(_>c%ea>dp(pb>dTTc>dDDd>d,e>d8ttf>d8ddg>cOhCdiCx @ jCHk>d\\v>dNs>d$$tC xx{>d@uC|}xDPBEPP.FI vQbRUltwdmoxxVTGSHJ p n y CH3OO  CH3 OO OH O CH3H ` tKd ` M ` hL|n `  W@   ` Y@ ` TXXB ` 8Nt4 CH3CH2O( H 4Zpp(Acetate ion: two contributing structures  0`0Ethoxide ion: no resonance ` Xz,4 ` ru ` ,fql0   \|\1/2o  ~dD41/2  4p<Resonance hydrid structureTimes'swsD Timesx! 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Q\Dd<d<   C AB?We[^TqFt T?We[^Tq0:\% _ nxZ}lu#Zs w<jbjb kkw8]R&&&&,R4& " $ $ $ $ $ $ ,P QP  !"#$%&'()*+,-./0123456789:;<=>?IJKLMNOTUVWXYZ[\]^_`abcdefghijklmnopqrstuvwxyz{|}~{;F{{{b" TT" {{  S" && Acids and Bases Skill List link to each section below Vocabulary Conjugate Acids and Bases Use of the pKa Table Molecular Structure and Acidity Vocabulary Discussion: Words in chemistry often have very precise meanings that are meant to convey specific concepts or relationships. It is important for you to be able to define these words in a precise and accurate manner, and provide examples where relevant. Understanding is much more useful than rote memorization. Exercises: Provide a precise definition for each word. Acid ionization constant Bronsted-Lowry acid Bronsted-Lowry base Conjugate acid Conjugate base Inductive effect Lewis acid Lewis base pKa link to exercise solutions Conjugate Acid and Bases Discussion: Proton transfers are key features of many organic and biochemical reactions. If a reactant accepts a proton (a Bronsted-Lowry base) the product is termed the conjugate acid of that base. An electron pair from the Bronsted-Lowry base is shared with the proton to make a new bond. If a reactant donates a proton (a Bronsted-Lowry acid), the product is the conjugate base of that acid. The electron pair that was the bond to the transferred proton is left behind as part of the conjugate base. As a fundamental skill necessary to master proton trasnfer reactions, you will need to be able to draw the conjugates of an acid or base. Example 1: Provide the products of the following proton transfer reaction. The proton that is transferred is circled. Label all reactants and products as Bronsted-Lowry or conjugate acids and bases.  Solution:  Example 2: A small portion of the molecules in liquid water have reacted by proton transfer. This process is termed autoionization. Write an equation for the autoionization of water that clearly illustrates this proton transfer. Name all the products. Label all reactants and products as Bronsted-Lowry or conjugate acids and bases. Solution:  Note that some compounds such as water in this example can function as either an acid or base. Such compounds are termd amphoteric. Where a compound is an acid or base is not controlled solely by molecular structure, but rather by the molecules role in the reaction. Exercises: Provide the products of each proton transfer reactions shown below. In each case, the proton that is transferred is circled. Label all reactants and products as Bronsted-Lowry or conjugate acids and bases.     e. The following proton transfer involves two steps. Can you figure out the structure of intermediates A and B?  Use of the pKa Table Discussion: The propensity of a compound to donate a proton is measured as its acid ionization constant, or Ka. These Ka values cover a wide range of 1010 for the strongest acids to 10-50 for the weakest acids. A more convenient scale of acidity is pKa which is the negative logarithm of the Ka. Thus a Ka of 1010 becomes a pKa of -10, and a Ka of 1050 becomes a pKa of -50. 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