Name: _______________

VERSION A Section: _________

TA name: ________________

Chemistry 237 Exam 1

CHEM 237A
February 7, 2014

Rules for this exam:

1. Work alone.
2. Allowed: one 3x5 note card with hand-written notes on the front and back, as
well as a model kit. No sharing of materials is allowed during the exam.
Anything used during the exam is subject to inspection.
3. Not allowed: Notes, phones, iPods / iPads, laptops / tablets, anything with an
internet connection, extra paper.
4. Please write on this exam. Show your work as completely as possible. Make
sure your answer is in the square provided. 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.
5. Remain seated until the exam is over.
6. No question is intended to trick you. If you are unsure about the instructions
on any question, please ask. Raise your hand if you have a question. Do not talk
to other students.

General Information:
This is a 45 minute exam.
There are 12 questions. Points possible are given on each problem.
TOTAL points = 100 possible
A periodic table is provided.
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1. Complete the Lewis Dot Structure for the structure of NCO-, below. Be sure to include lone
pairs, formal charges and add any important resonance structures. (4 points)

2. Draw a correct Fischer Projection for (2S,3R)-2-chloro-3-bromopentane. The carbon

backbone of the projection has been drawn for you; please use it. (4 points)

3. What is the IUPAC name of the compound below? Show your carbon-chain numbering on
the picture. (4 points)

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4. Draw the most stable chair conformation (side-on projection) for each of the following
molecules. Assume CH3 is bigger than Cl. (5 points each)

A: B:

a. At equilibrium, which one (A or B) would have the largest proportion of conformers with Cl in
the axial position? (4 points) ________________

b. What is the stereochemical relationship between the two molecules? Circle one answer. (4
points)

A. Enantiomers C. Conformational Isomers

B. Diastereomers D. Constitutional Isomers

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5. For each set, circle the molecule that has the indicated relationship to the molecule in the
box (5 points each).

a) is a diastereomer of:

b) is an enantiomer of:

6. Draw the structures of the organic products that would result from the free-radical
halogenation of the following compounds. Assume only mono-halogenation. (8 points)

a) Methylcyclohexane and Br2 (1 product)

b) 2,4,-dimethylpentane and Cl2 (3 products)

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7. Circle each of the molecules below that would produce an energy diagram like the one
shown for rotation of the bond in bold (note: CH3, Br, and Cl are different sizes). (3 points for
each correct answer circled; -3 for each incorrect/missing answer)

8. Complete the following acid/base reaction by filling in the products of the reaction. Calculate
the approximate Keq of the reaction using approximate values for each acid. (9 points)

Keq =

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9. Lovastatin is one of the first drugs marketed for the purpose of reducing cholesterol. It is a
naturally occurring product found in oyster mushrooms. Place a star next to all the chirality
centers in the structure of Lovastatin, below. (+1/2 for each correct center, -1/2 for each
incorrect / missed center; no negative scores)

10. Which of the following are correct Fischer Projections for the following molecule? You may
circle more than one answer. (+3 for each correct structure, -3 for each incorrect / missed
structure; no negative scores)

/13
11. Circle and identify the functional groups in the molecule below (Atorvastatin, the active
ingredient in Lipitor). Be sure to circle all the relevant atoms involved in the functional groups.
(+2 for each correct group, -2 for each incorrect / missed group; no negative scores)

12. Pairs of structures are shown below. For each pair, indicate whether they are a) identical, b)
resonance forms, c) constitutional isomers, d) stereoisomers, or e) conformational isomers. (3
points each)

A) B)

C) D)

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TOTAL: /100
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