Your preparation for the lecture and laboratory section:

Get a lab notebook (you can use the one from Chem 30AL if you still have pages left), a flame-resistant lab coat, goggles and nitrile gloves (the blue or purple version, 4 mil will do fine, see here) before you come to the lab i.e., AXE (YH1275). The first lecture will be held on Monday, March 28, 2016 at 3 pm in CS 76. Please make sure to show up on time even though the lecture is scheduled to be podcasted this quarter as well (recording can be found on the OID website, usually the day after the lecture took place (if not, please inform the instructor, who can follow up on any problems), you will need a Bruin ID to access it).

The labs will start on Tuesday, March 29, 2016 at 1:00 pm (for those of you that are enrolled, wait-listed or plan to get enrolled in these lab sections (1 A and 1 B, waitlisted or adding to class). Make sure to be properly dressed and to bring your lab coat (knee-length flame-resistant coat are required due to CAL OSHA rules, no cotton or polyester lab coats are acceptable), goggles, closed-toe shoes and nitrile gloves with you because you will handle chemicals on the first day already. If you do not show up properly dressed, you will not be allowed to conduct the lab, which means that you will be dropped from the course. Attendance during your first meeting is mandatory. If you do not attend during the first 15 minutes, you will automatically lose your spot in the course because wait-listed and other students will get enrolled then. Wait-listed students will be signed up then based on priority (Chem & Biochem majors first, then according to seniority, extension students are at the end of the line. Sorry!). Nobody enters the lab before being approved by the instructor because this will make it easier to sort everything out quickly.

Required texts are the Course Reader (Organic Chemistry 30BL Reader, Spring 2016), the techniques and spectroscopy reader ("A Short Survival Kit for O=Chem Lab", Spring 2016), the Exam Collection Reader for Chem 30 BL (Spring 2016). The textbook from J. Mohrig et al. (Techniques in Organic Chemistry, 4^th edition) is recommended. The course reader package is available at Course Reader Materials in Westwood (1081 Westwood Boulevard) starting March 21, 2016. They are usually open from M-F 9-4 pm (phone number: (310)443-3303). It is in your best interest to have the latest edition of the readers, since this is the source your TA and the instructor use for lectures, quizzes and exams. The readers overwent revisions over the summer, so the old readers will not be useful. The package is about $65 and this is be the wrong place and time to save a few dollars. Look at it as an investment of passing the course by having the up-to-date information available to you. However, it will also be necessary to look at them and not just use them as a door stop!

The final exam will be administered on Friday, June 10, 2016, 8:00-11:00 am, room tba. There will be no make-up exam! So plan your final exam schedule accordingly! If you plan to take the final exam with OSD, please make sure to make arrangement with them early since seats are limited there. The instructor will not be able to administer the exam for these students due to the limited resources.

Lecture attendance is mandatory. There might be a pop quizzes throughout the class in lecture. It is also highly advisable to read the lecture material and powerpoint slides before hand since it makes it easier for you to understand the material covered in lecture. The lecture time allotted for this class does not permit to discuss every little aspect of this class in great detail. You will be held responsible to read up on certain aspects on your own in the readers and other sources. The instructor will offer additional work-shops on Mondays (5-6:30 pm, room and start: tba) to review spectroscopy (Infrared, NMR, UV-Vis) and other topics of interest starting (Topic of workshop 1: Introduction to Infrared Spectroscopy, you will need the Survival Kit reader then!). The spectroscopy workshop will be podcasted as well.

Please make sure that you registered a working email address with URSA and that you actually check it on a regular basis meaning at least once a day. The instructor frequently uses this method of communication to make general announcements and inform students about changes and other topics.


1. Check-in

Before you come to the lab, make yourself familiar with the names and function of the equipment (see reader and website) that you will use during this lab course. It will make it easier for you to communicate with your teaching assistant and/or instructor during the check-in procedure and throughout the laboratory course. Please make sure to read the syllabus and any additional material pertaining to the experiment in the lab as well.

Important pieces of glassware i.e., conical vials, the Hickman head, and the air condenser should be crack free. Conical vials have to have a ground glass joint, which allows the condenser or Hickman head to fit in there. If you have a Hickman head with a side port, make sure that you have the appropriate compression cap and flat septum as well. If not, try to obtain it from the lab support (YH 1072, window on the right side) or exchange it. Some pieces of the glassware (i.e., beakers, Erlenmeyer flasks) might have a minor chip at the top, which usually does not interfere with their functionality. Be very carefully when handling glassware since it can break which can cause deep cuts! If you are in doubt, ask your teaching assistant. Place all extra glassware at a location previously determined by the teaching assistant i.e., hood or designated bench or bin. It is very likely that one of your fellow students is missing it. This speeds up the check-in process significantly, because you and your fellow students might not have to stand in the long line in front of the lab support to get the missing glassware.

The instructor and/or the teaching assistant will discuss different aspects of safety before you start your in-lab work. It is very important that you are aware of the dangers in this laboratory course. This does not mean that you have to freak out handling chemicals. In this course you will encounter more dangerous chemicals than in general chemistry. Some of them are very corrosive i.e., concentrated acids and bases, and some of them are highly flammable i.e., diethyl ether or other organic solvents. It is part of your preparation to inform yourself about the hazards of a particular compound that you will be using and how to handle it properly in the lab. It is important to develop a consciousness for safety in order to be safe and efficient in the lab. The teaching assistant will show you where the safety related equipment i.e., emergency shower, eye wash, and fire extinguisher is located, and how it is used. Whenever possible try to place your setup underneath the shelf in the middle part of the bench. It is connected to a ventilation system that will remove the majority of the evolved fumes. Proper clothing (closed-toed shoes, low heels, long pants, shirts or sweaters with long sleeves, a lab coat (as described above), goggles and gloves) is still the best protection if an accident does occur and you plan on getting through this lab course unharmed. The proper dresscode will be strictly enforced in this course to ensure your own safety. If you are seen without goggles, the teaching assistant will take off points from your in-lab evaluation. If you wear sandals, shorts, short skirts, etc., you will be sent home immediately, which means that you will not be allowed to take the quiz and also will lose 10 points for your in-lab evaluation since this shows very poor preparation.

The teaching assistant will discuss the specific format of the post-lab reports. Please make sure that you read the appropriate chapter in the reader before hand. If something is not clear, feel free to ask the teaching assistant or instructor. Bottom-line is that the pre-lab report should show that you have a clear understanding about the experiment that you are about to perform in the lab. Copying from the reader or prelabs from your friends alone is not enough! The post-lab write-up has to demonstrate that you are able to explain your observations and can analyse the obtained data correctly. There are many students who do well in the lab (based on their scores in the reports) and end up getting poor grades in the class, because they just copied reports from friends/roommates/etc. The exam will show if you mastered the material or not. A score below than 50 % in the final exam or/and an unsatisfactory performance in the lab, will result in a grade lower than a "C-"-grade. Attendance in the lab and during the final exam is not sufficient to warrant a "C-"-grade or higher!

For the first meeting only you will be allowed to use the reader. Afterwards, you will be deducted points because the use of the reader shows that you are not prepared enough for the lab section. You should include all the information that you need to perform the experiment in the lab in your pre-lab i.e., infrared data, physical properties, etc. This rule applies already in meeting 2, which means that you will have to prepare the entire prelab for meeting 1 and meeting 2 for the second meeting.


2. Coenzyme Synthesis of Benzoin

General comments:

You will also have to start the coenzyme synthesis during meeting 1 (and finish it up during meeting 2. Prepare a pre-lab for the entire experiment by then because you will not be allowed to use the reader anymore!). It will be the first step of a multistep synthesis project that will follow you throughout the course. During meeting 4, you are going to oxidize benzoin to benzil using bleach. After an aldol condensation (leading to 1,2,3,4-tetraphenylcyclopentadienone, TPCP), the final product of the sequence will be 1,2,3,4-tetraphenylnaphthalene (TPN). It is imperative that you get a good yield in all of these steps in order to be able to receive a reasonable yield for the final product of this project. You will also use benzoin in the last experiment (Grignard reaction). So please make sure that you get a decent quantity (~1.5 g) of the product.

Experiment:

1. The addition of NaOH (2N) should be done slowly in order to avoid an excess of base. Why? The color only has to change from yellow to pale yellow.

2. Make sure that you have a homogeneous mixture after you added the benzaldehyde.

3. Make sure that you close the vial properly to reduce the oxidation of the benzaldehyde (the 6-dram vial should be in your desk already. If not, please get one from lab support and keep it after the experiment is completed because you will need it for other experiments).

4. You should come back the next day and check if crystals have formed. If not, scratch the inside of the vial to initiate the crystallization. If you do not obtain a solid after scratching and cooling, consult your teaching assistant. If s/he cannot help you, try to consult the instructor as well before you discard the mixture.


3. Critical Thinking

a. Why does the benzaldehyde have to be fresh for the coenzyme synthesis?
b. How does "old" benzaldehyde differ from "fresh" benzaldehyde?
c. How does the scratching the inside of the flask promote the crystallization process?
d. Why is the mixture placed in an ice-bath before isolating the product?
e. What is an ice-bath?
f. Benzaldehyde is a liquid while benzoin is a solid. How can the difference be rationalized?