Introduction

These errors have been discovered by students and are listed here for your convenience. Sometimes errors are corrected between subsequent printings of the same edition of a text.  Because of this you may not see some of the errors listed below. If you find more errors, please bring them to my attention by email.

My thanks to the students who have brought these errors to my attention.

The errors on this list are true typographical errors, not differences in style. For example, these texts contain a number of naked protons (H⁺).  Although I strongly prefer that you use H₃O⁺ instead of H⁺, any naked protons in these texts are generally not considered errors.

Not all errors are listed here. Errors in web site content (exam keys, OWLS solutions, etc.) are usually handled by posting a revised version of the erroneous document.

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• Vollhardt and Schore (6^th edition) and Study Guide
• Brown, Foote, Iverson, and Anslyn (5^th edition): Complete textbook    Custom edition for UCLA
  
• Brown, Foote, Iverson and Anslyn solutions manual 5^th edition (for complete or custom edition of textbook)
  

• Chemistry 14C Thinkbook, 2011 edition
  
• Chemistry 14C Lecture Supplement, 2011 edition
  
• Chemistry 14D Thinkbook, 2011 edition
• Chemistry 14D Lecture handouts
  
• Chemistry 30B Thinkbook
  

• Organic Chemistry as a Second Language, 3^rd edition (Klein)
  

• All courses

• Entire textbook
• Many mechanisms show protons departing without a base to remove them. A proton never falls off by itself; some base (B) must remove it. The resultant conjugate acid (B-H) is often not included in a mechanism, but you can include it for the sake of completeness. Some mechanisms also show protonation without the corresponding curved arrows, and with (gasp!) naked protons (H⁺).
• Chapter 1
• Section 1-4, page 14: Then subtract supply from demand and divide by 2.
• Chapter 2
• Table 2-2, page 60: Hydronium ion has a formal positive charge (H₃O⁺) not a formal negative charge.
• Chapter 5
• Page 172, last paragraph: All the chiral examples contain an atom that is connected to four different groups. (Delete 'substituent', because hydrogen atoms are not considered to be substituents.)
  
• Chapter 6
• Page 218, first full paragraph: Table 6-3 depicts methyl, primary, and secondary (but not tertiary) halides.
• Page 228, first paragraph: The generally accepted explanation for nucleophilic backside attack and the stereochemistry of the S_N2 reaction is that the nucleophile attacks the sigma* (antibonding) orbital associated with the carbon-leaving group bond, and not the small sigma (bonding) orbital backlobe associated with the carbon-leaving group bond. (The stereochemical outcome of these reaction pathways is identical, but the thermodynamics are different.)
  
• Page 238: At the bottom of the page: water has two lone pairs, not three.
• Chapter 7
• Table 7-2, page 261: In the entry for S_N2 reaction at a tertiary carbon, change "extremely slow" to "no reaction." Because S_N2 reactions at tertiary carbons are virtually unknown, we might accept either rate, but "no reaction" is more consistent with the discussion of this idea in Chapter 6.
• Page 259, middle reaction scheme: The correct formula for calcium formate is Ca(OC=OH)₂ or (HCO₂)₂Ca.
  
• "E2 Reactions Proceed In One Step", page 267: This is a false generalization. In every E2 reaction the C-H and C-LG group bonds are broken simultaneously. However, we can imagine a circumstance in which the base must be deprotonated before the elimination event occurs. In this case, the reaction still follows E2 kinetics, but is not concerted.
• Chapter 10
• Exercise 10-5(a), page 399: The correct structure is CH₃CH₂OCH₂CH₃.
• Page 409, last paragraph, third line: The correct name is 1,1-dichloro-2,2-diethoxyethane.
• Exercise 10-13B, page 412: The first ¹H-NMR signal has a chemical shift of 0.93 ppm.
• Chapter 12
• Page 521, Mechanism for Formation and Nucleophilic Opening of a Cyclic Bromonium Ion: The first mechanism step is missing a curved arrow depicting the formation of the second carbon-bromine bond. The correct mechanism step is:

• Page 530, paragraph under alkylborane oxidation mechanism: The process is repeated until all three alkyl groups have migrated to oxygen atoms, finally forming a trialkyl borate (RO)₃B.
  
• Chapter 14
• Figure 14-15, page 652: λ_max = 222.5 nm
• Chapter 15
• Page 685, first paragraph: The benzene ring protons do not all couple with each other. The ortho protons are equivalent, and do not couple with each other. The same is true for the meta protons.
  
• Chapter 15
• Page 704, Bromobenzene Formation: The curved arrow which begins at a bromine lone pair should begin at the iron-bromine bond.
• Page 705, Activation of Nitric Acid by Sulfuric Acid: HONO₂ is protonated by H₃O⁺, not H₂SO₄.
  
• Page 706, Mechanism of Aromatic Sulfonation: A proton (H⁺) does not fall off of a molecule by itself, even if its loss from an arenium ion restores aromaticity. A base of some sort removes the proton. In this mechanism the base is either SO₃ or PhSO₃^-.
• Page 709, Mechanism of Friedel-Crafts Alkylation: In step 3, the carbon at the six o'clock position of the ring is missing its positive formal charge. In addition, the curved arrow which starts at a one pair on X should begin at the X-Al bond.
• Page 713, solution 15-31: In the final mechanism step, the curved arrow which starts at a one pair on Cl should begin at the Cl-Al bond.
• Page 719, solution 15-32: The correct formula for DDT is C₁₄H₉Cl₅.
• Chapter 26
• Page 1214, increasing pH diagram: pH ? 6 should be pH = 6.
  
• Appendix: Answers to Exercises
Solution 6-10, page A-10: The correct units are L mol^-1 s^-1 or M^-1 s^-1.

• Entire study guide
  
• Many mechanisms show protons departing without a base to remove them. A proton never falls off by itself; some base (B) must remove it. The resultant conjugate acid (B-H) is often not included in a mechanism, but you can include it for the sake of completeness. Some mechanisms also show protonation without the corresponding curved arrows, and with (gasp!) naked protons (H⁺).
  
• The study guide contains numerous sloppy curved arrows, with ill-defined or misleading start and/or ending positions.
  
• Chapter 1
• Solution 26(i), page 5: The H-N bond is polar: δ⁺ H-N δ^-.
• Solution 43(c), page 16: The correct bond-line structure is:

• Solution 46(c), page 18: Each oxygen atom in this answer has two lone pairs.
• Chapter 2
• Solution 45, page 37: The structure of chrysanthenone is the enantiomer of the structure given in the text.
• Chapter 4
• Solution 45, page 73: Cortisone is missing two methyl groups. The corresponding structure given with the problem in the textbook is correct.
  
• Chapter 8
• Solutions 23-25, page 151: Solution 23 is actually the solution to problem 24; solution 24 is actually 25, and 25 is actually 26. Solutions numbered 27 and beyond on pages 152 and beyond are correct.
• Chapter 12
• Discussion of sections 12-13, page 242: The second step in the free radical addition of HBr to propene is missing the second curved arrow in the H-Br bond scission (the curved arrow that shows one electron of the bond going to the bromine atom).
• Solution 67(b), page 262: The first step in the mechanism for addition of Cl₂ to an alkene is:

• Chapter 15
• Solution 51, page 307: In the last step, the leaving group is Cl^- (not C).
• Chapter 17
• Solution 38(a), page 337: The curved arrows that shows proton transfer from CH₃OH to the tetrahedral adduct is missing.
• Glossary
• Overall the glossary contains numerous falsely restrictive or falsely general definitions. Ignore it. Use the Illustrated Glossary of Organic Chemistry instead.
  

• Chapter 1
• Page 3, Rule 3: The ground state configuration for carbon is 1s² 2s² 2p_x¹ 2p_y¹ 2p_z⁰.
• Page 23, first paragraph: the predicted H-O-H bond angle is 109.5^o.
• Page 36, sp hybridization diagram, middle of the page: change sp² to sp.
• Page 50, Table 1.11: The data for acetylene is absent. Acetylene is the simplest alkyne, consisting of a carbon-carbon triple bond, with each carbon having a C-H sigma bond. The two C-C pi bonds are constructed by overlapping a pair of 2p orbitals for each pi bond. The C-C sigma bond comes from the overlap of two carbon sp orbitals (one from each carbon), and the C-H sigma bonds from the overlap of a carbon sp orbital with the H 1s orbital. The C-C bond length is 120.3 pm and the C-H bond length is 106.0 pm. The C-C bond strength is 966 kJ mol^-1 (231 kcal mol^-1) whereas the C-H bond strength is 556 kJ mol^-1 (133 kcal mol^-1).
• Chapter 2
• Page 95, start of second paragraph: 0.08-8 kJ (0.02-2 kcal) per (or /) mol
  
• Chapter 5
• Solution 5.6(c), page 190: The correct name is 1-methyl-4-(1-methylethyl)-cyclohexene.
  
• Chapter 6
• Page 206: In this chapter, the mechanisms involve carbocation intermediates where carbon has three bonds and only six valence electrons, as is positively charged (see Section 6.3A).
• Page 221: The very first mechanism step on this page is missing a curved arrow which shows carbon-bromine bond scission.
• Page 230: In step 3, CH₃CH=CH₂ + 2 H⁺ + 2 e^- ---> CH₃CH₂CH₃.
• Table 6.2, page 237: The correct structure of ethylene is H₂C=CH₂ (or less precisely CH₂=CH₂).
  
• Page 245, Key Reaction 1: HX is used to convert alkenes into haloalkanes in an...
• Problem 6.27, page 250: The question states the solvent is carbon tetrachloride (CCl₄) whereas in the reaction scheme it is dichloromethane (CH₂Cl₂). Either solvent can be used, but they must be consistent between the problem statement and the reaction scheme.
• Chapter 11
• Page 426, Acid-Catalyzed Cleavage by Concentrated HX: Reaction of dibutyl ether with 2 moles HBr gives two moles butyl bromide plus one mole H₂O.
• Page 447, Key Reaction 11: Change the 9 into a carbon-carbon bond.
  
• Chapter 12
• Page 458, calculations near bottom of page: In the 400 cm^-1 calculation, change 10^-1 m to 10^-2 m.
• Page 472, section 12.3 summary: The vibrational infrared region extends from 2.5 x 10^-6 m to 2.5 x 10^-5 m.
  
• Chapter 14
• Page 523, last paragraph: Use the data in Table 14.2, not 14.1.
• Page 533: The diagram in the middle of the page is a repeat of the diagram above it; it is not an example of the McLafferty rearrangement.
• Chapter 16
• Page 584, Step 2 box: The base is HO^- not H₂.
• Page 596, Mechanism step 2: The second structure is missing an R group.
• Chapter 25
• Page 984, top figure, last structure: The axial hydrogen atom of C3 has been omitted. (This is not an error, because hydrogen atoms do not have to be drawn when the carbon atom is not specified with the letter C; however it is a confusing stylistic difference between this structure and the other structures in the same figure, wherein this hydrogen atom **is** included.)
  

• Chapter 1
• Page 49, first line of text: ...the three delocalized molecular orbitals of Figure 1.26.
  
• Chapter 2
• Table 2.7, page 98: The heat of combustion of octane is -5470.6 kJ/mol.
• Problem 2.16(a), page 104: The structure shown has a pentavalent carbon. The correct structure is:

• Chapter 6
  
• Table 6.2, page 237: The correct structure of ethylene is H₂C=CH₂ (or less precisely CH₂=CH₂).
• Problem 6.27, page 250: The question states the solvent is carbon tetrachloride (CCl₄) whereas in the reaction scheme it is dichloromethane (CH₂Cl₂). Either solvent can be used, but they must be consistent between the problem statement and the reaction scheme.
  

• Chapter 2
• Solution 2.7(d): The molecular formula of bornane is C₁₀H₁₈.
• Chapter 6
• Solution 6.34(a): The alkene is protonated by H₃O⁺, not by H₂SO₄.
• Chapter 9
• Solution 9.22(a), page 187: The by-product of this reaction is HCl, not HBr.
• Chapter 10
• Solution 10.28(b), page 221: Oxygen (EN = 3.5) is more electronegative than chlorine (EN = 3.0).
• Solution 10.28(c), page 221: Resonance has more influence on the pK_a of a carboxylic acid versus an alcohol than inductive effects.
• Solution 10.43, page 235: In step 2, the curved arrow showing scission of the carbon-tosylate bond needs to start at the bond, not at the tosylate lone pair. The correct curved arrow is:

• Chapter 14
• Solution 14.11: The corresponding probability that a given carbon atom is ¹²C is 100/(100 + 1.11) = 0.989.
• Solution 14.22: For C₆H₁₂O M has m/z =100 (not 88).
• Solution 14.24: The probability that both chlorine atoms are ³⁵Cl is (0.7557)² = 0.5741.
• Solution 14.24C, page 303: [³⁷ClCH_²CH₂]^+. has m/z = 65.
• Solution 14.33C, page 308: [CH₃CH₂CH₂CH₂CH₂]^+. has m/z = 71.
• Solution 14.37, page 309: The correct chemical formula for THC (tetrahydrocannibinol) is C₂₁H₃₀O₂.
  

• Molecular Structure: Introduction and Review
• Practice Problem 21, page 12: The ester of the molecule in question 15(b)...
• Practice Problem 22, page 12: ...Xenical (question 15c)...
  
• Practice Problem solution 5(c), page 19: Delete the "In addition..." sentence.
• Practice Problem 46(a) solution, page 34: The C-C-C bond angles of cyclobutane are 90^o when planar, or a bit less when cyclobutane is puckered.
• Resonance
• Practice Problem 14, page 48: Resonance plays an important role in the structure and function of the four DNA nucleobases: Thymine, cytosine...
  
• Biomolecules Survey Part 1: Carbohydrates
• Concept Focus Question solution 5, page 108: The given answer doesn't cover ketoses. Add this line: When the molecule in question has a CH₂O group on each carbon adjacent to the ring oxygen, remember that an aldose anomeric carbon must have a hydrogen atom whereas a ketose anomeric carbon cannot have a hydrogen.
• Practice Problem 14, page 111: Delete this problem.
• Practice Problem solutions, page 112-116: There are some numbering errors. The corrected version can be found here (pdf).
• Practice Problem solution 11(b), page 114: Humans can readily digest carbohydrates that have α stereochemistry...
• Practice Problem solutions 19 and 20, page 115: Delete these solutions.
  
• Mass Spectrometry
• Concept Focus Questions solution 10, page 119: Should be numbered as solution 8.
• Concept Focus Question solution 8, page 121: Should be numbered as solution 9.
  
• Concept Focus Question solution 10(b) [actually solution 8(b), when numbered correctly], page 120: M has m/z = 157 (not 158). The calculations should be changed according, resulting in two acceptable formulae: C₈H₁₂ClN and C₉ClN.
• Practice Problem solution 8, page 128: The formula has seven carbons, or (less probably) eight carbons.
  
• Practice Problem solutions 9 and 10, page 128: These answers are switched.
• Proton NMR Spectroscopy
• Practice Problem solution 8(e), page 168: For 1.39 ppm, add the implication 2 x CH in (CH₂)₂CHCH.
  
• Solving Spectroscopy Problems
• Practice Problem 16, page 181: The following molecule is a good guess for the final structure of problem 11...
  
• Practice Problem solution 2, page 184: For zone 1, terminal alkyne: Absent - no peak; no DBE.
• Practice Problem solution 2, page 185: For 1.61 ppm, add the implication 2 x CH in (CH₂)₂CHCH. For the same chemical shift, change 2 x CH in CH₂CH(CH)₂ to 2 x CH in (CH)₂CHCH₃.
  
• Practice Problem 2 solution, page 185: For 1.61 ppm change the last implication to 2 x CH in CHCH(CH₂)₂. In the pieces list, the last piece is CH₃ in CH₃CH₂.
• Practice Problem 4 solution, page 188, 1.8 ppm implications: Change 2 x CH in CH₂CH(CH)₂ to 2 x CH in CH₃CH(CH)₂. Also add implication 2 x CH in (CH₂)₂CHCH.
  
• Practice Problem 5 solution, page 190, 1.3 ppm implications: Add the implication 2 x CH in (CH₂)₂CHCH.
• Practice Problem 6 solution, page 192, 1.3 ppm implications: Add the implication 2 x CH in (CH₂)₂CHCH.
• Practice Problem 7 solution, page 194: For 4.49 ppm, add the implication CH in (CH₂)₂CHCH. For 1.95 ppm add the implication 2 x CH in CH(CH)₃.
  
• Practice Problem 9 solution, page 198, 1.3 ppm implications: Add the implication 2 x CH in (CH₂)₂CHCH.
• Practice Problem 10 solution, page 200: For 3.47 ppm implications add the implication CH in (CH₂)₂CHCH. For 1.73 ppm add the implication 2 x CH in CH(CH)₃.
• Practice Problem 12 solution, page 205: For 1.12 ppm the implications are 2 x CH₃, 3 x CH₂, and 6 x CH.
  
• Practice Problem 14 solution, page 209, 2.9 ppm implications: Add the implication CH in CH₂CH(CH)₂.
• Practice Problem 15 solution, page 211: For the 1.8 ppm ¹H-NMR implications, add CH in CHCH(CH₃)₂. In the pieces list add one DBE (probably a ring).
• ¹³C-NMR, 2D-NMR, and MRI
• Practice Problem 16 solution, page 234: For 1.68 ppm add the implication 2 x CH in CH₂CH(CH)₂.
• Introduction to Structure and Reactivity: Organic Acids and Bases
• Practice Problem 15 solution, page 280: In the very first Discussion section on this page, in the sixth line: "...force to share electron density."
  
• Practice Problem 18 solution, page 281. In the last line: "Removal of resonance is a destabilizing factor, making it harder to protonate aniline than to protonate ammonia."
  
• Biomolecules Survey Part 2: Lipids
• Practice Problem 7 solution, page 305: The correct structure for Bruinane is:

• Molecular Structure: Introduction and Review
• Page 3, bottom slide: The correct structure for cholesterol is:

• Mass Spectrometry
• Page 108, bottom slide: Change 102 (C₆) to 72 (C₆).
• Infrared Spectroscopy
• Concept Focus Question 7, page 112: The molecule's formula is C₆H₁₂O₂.
• Proton NMR Spectroscopy
• Page 157, top slide: The field lines for the magnetic field produced by the pi electrons are backwards. The field should sprout from the bottom and flow upwards.
  
• Amino Acids, Peptides, and Proteins
• Page 240, top slide: The correct three-letter abbreviation for asparagine is Asn.
  

• Electrophilic Aromatic Substitution Lecture Supplement
• Page 27, bottom slide: The title correct title is So What Is Up With Benzene?
• Radicals Lecture Supplement
• Page 45: The correct structure for ascorbate is:

• Ionic Substitution Reactions - S_N2
• Question 38, page 101: How does the k₁/k₂ ratio change...
• Practice Problem solution 3(b), page 101: The correct reaction product is CH₃CH₂OH.
• Practice Problem solutions 38 and 39, page 114: Solution 38 belongs to problem 39, and solution 39 belongs to problem 38.
• Practice Problem solution 38 (numbered as 39), page 115: In the third paragraph: The reaction with k₂ starts with charged reactants... Also: Water (ε = 80) is more polar than acetone (ε = 21)... Also: In the transition states the alkyl group attached to the carbon undergoing substitution is CH₂(CH₂)₅CH₃.
• Ionic Substitution Reactions - S_N1
• Practice Problem solution 19(b), page 136: The second product (identical to the starting material) is extraneous, and should be deleted.
• Practice Problem solution 24(b), page 140, last paragraph, second sentence: This does not automatically mean the reaction must be S_N1 by default...
• Practice Problem solution 29(e), page 143: For consistency with the other parts to this problem, the structure is missing the dotted line which indicates the site of fragmentation.

• Elimination Reactions
• Practice Problem 28(a) solution, page 173: E1 and S_N1: Good leaving group, polar solvent and secondary carbocation intermediate.
• Addition Reactions of Carbon-Carbon Pi Bonds
• Practice Problem 21 solution, page 203: The last paragraph beginning with "Vinyl carbocations..." and the reaction scheme below this paragraph belong to Practice Problem solution 22.
• Electrophilic Aromatic Substitution
• Concept Focus Question 3 solution, page 209, in the first paragraph: A reasonable, alternate mechanism uses a bromine cation...
• Radicals
• Concept Focus Question solution 7, page 241: Freons may also include hydrogen.
• Practice Problem 27, page 248: Very briefly outline the role played by chain reactions and antioxidants...
• Practice Problem solution 28, page 261: The correct structure for ascorbate is:

• Carbonyl Chemistry - Survey of Reactions
• Concept Focus Question 2(b), page 281: Delete this question.
• Concept Focus Question 1(c) solution, page 282: The oxonium ion deprotonation occurs in the second step of the reaction mechanism.
• Concept Focus Question 2(a) solution, page 283: The correct mechanism is:

• Practice Problem 13, page 294: The correct structure of acetyl-CoA is:

• Practice Problem 14, page 295: Change the thiol product (RSH) to the corresponding thiolate (a thiol's conjugate base, RS^-).
• Practice Problem solution 1(h), page 298: In the third resonance contributor, none of the oxygen atoms has a formal charge.
• Practice Problem 3(i) solution, page 302: Add this text to the start of the first paragraph below the mechanism: To move the mechanism forward the first tetrahedral intermediate would have to eject O^2- as the leaving group (very bad), so...
• Practice Problem 13 solution, page 310: The correct structure of acetyl-CoA is:

• Practice Problem 14 solution, page 310: Change the RSH product to RS^-. (RSH pK_a 10; H₂O pK_a 15.7, so the protonation of RS^- by H₂O is disfavored.)

• Elimination Reactions
• Page 9, second slide: The product of the E2 reaction between 2,2-dibromobutane and ^-NH₂ is missing a bromine atom. The correct reaction scheme is:

• Infrared Spectroscopy
• Question 8, page 151: The formula is C₁₂H₂₄O.
• Solution 8, page 156: The solution is correct; the error lies within the problem.
• Proton NMR Spectroscopy
• Solution 8, page 163: The solution should also include a statement concerning the benzene ring 'gated community' restriction.
• Solving Spectroscopy Problems
• Question 2, page 186: Add this clue: The molecule does not contain an oxygen-oxygen bond.
• Alcohols and Ethers
• Solution 6(a), page 254: K_eq < 1.
• Solution 9(a), page 256: In the absence of water, an acidic Cr⁶⁺ reagent oxidizes a primary alcohol into an aldehyde. In the presence of water, an acidic Cr⁶⁺ reagent oxidizes a primary alcohol or an aldehyde into a carboxylic acid.
• Solution 12(c), page 258: The last two structures in the mechanism are missing a methyl group next to the oxygen atom.
• Solution 21(a), page 260A: The mechanism shown belongs to question 20. The correct Payne rearrangement mechanism is:

• Carbonyl Chemistry - Fundamentals
• Solution 9, page 282: In the steric effects paragraph, change 'empirical date' to 'empirical data'.
• Carbonyl Chemistry - Survey of Reactions
• Question 17, page 311: 11-Cis-retinal is derived from vitamin A.
• Solution 11, page 324: Route B is the most efficient route.

• Chapter 2
• Solution 2.47, page 352: The carbon that started as part of the C=N bond should have a positive formal charge.
  

No uncorrected errors reported so far.