Name:________________________________________

Section/TA:____________________________________

Mid-quarter Exam 2
CH 237A
November 16, 2012
You have 50 minutes to complete the exam.
When time expires, you are required to close your exam and hand it in.
You are allowed one 3x5 note card with hand-written notes on the front and back,
and a model kit. No sharing of materials is allowed during the exam. Anything used
during the exam is subject to inspection.
You must turn in your exam before leaving the room. No back-and-forth.
You may use the back of any page as scratch paper, but make very clear (i.e.,
circle) the answers you want graded if you do so.
You may use only black, blue, or purple ink. You may also use pencil.
No question is intended to trick you. If you are unsure about the instructions on
any question, please ask.
You should have 9 pages total.

Problem

Points

/ 30

/ 15

/ 33

/ 30

/ 15

/ 30

Total

/ 153
1

Name:________________________________________
Section/TA:____________________________________

1)

Provide the missing starting materials or products in the boxes. You should only
draw one major isomer/product in each case. For products, provide only the
major organic product. You may use any projection that conveys the correct
stereochemistry where applicable. (5 points each)

Name:________________________________________
Section/TA:____________________________________

2)

Provide an arrow-pushing mechanism for ONE of the two reactions shown

below. You get to choose. If you attempt each, make clear what work you want
graded. (15 points).

Name:________________________________________
Section/TA:____________________________________

3)

The mechanism below has all structures that are needed, but in incomplete
form. You must fill in the MISSING ARROWS and ANY FORMAL CHARGES.
(3 points each correct arrow/charge, -2 points for each incorrect arrow/charge).

4) Provide a multistep synthesis for the two syntheses shown below. Full

credit requires a completely correct forward synthesis. This will earn full
credit even without any retrosynthetic work. However, you may receive
partial credit for showing retrosynthesis.

Name:________________________________________
Section/TA:____________________________________
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Name:________________________________________
Section/TA:____________________________________

Complete the reaction coordinate diagram (RCD) below and use any additional
drawings or text to provide an explanation for why Zaitsevs rule is observed
during E2 eliminations. Include a description of any transition state or
intermediate structures. As a starting point, a simple example reaction is
provided below. The starting alkyl chloride has been placed on the RCD
already, as well as reference points for each product. (15 points)

energy

5)

reaction coordinate

Name:________________________________________
Section/TA:____________________________________

6)

The reaction depicted below is known as a dihydroxylation. Answer the

following questions that would be used to determine if the reaction proceeds via
a syn, anti, or nonspecific addition mechanism? (30 points)

Which of the following alkenes would be most useful for determining if a

carbocation intermediate is involved (circle it)? Explain your reasoning.

Which of the following alkenes would be most useful for distinguishing between
syn and anti addition mechanisms (circle it)? Explain your reasoning.

Name:________________________________________
Section/TA:____________________________________
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