1 (20 points). A bottle sits in your freezer. The label is only partly legible.

It
reads either: cis-1,2-dmethylcyclohexane (schematic A) or cis-1-ethyl-2methylcyclohexane (schematic B). You measure the optical rotation and note
that it does not change as the temperature rises to room temperature. Is the
molecule A or B? Explain in detail, please, and note that you cannot answer
this question in two dimensions or with the schematic structures given.

2 (10 points). You have a bottle labeled 1,1,2,3-tetramethylcyclopropane,

but the first word in the name has been scraped away. It is either cis- or
trans-. Your NMR machine tells you that the molecule in the bottle has 5
different carbons. Is the compound cis or trans? Explain briefly how you
knew. In your answer be sure to number each of the five different carbons.
The structure below is only a two-dimensional sketch of the molecule.
CH3
H3C

H3C
CH3

3 (16 points). Make three-dimensional drawings of all the stereoisomers of

the following two molecules. Label each as either (R), (S), (E), (Z) or some
combination. You only have to do 3D on the critical portions of the molecules
the parts that might be (R), (S), (E), or (Z). Dont render every irrelevant
CH2 or CH3 in 3D.

4 (30 points). Once again, you have a bottle containing a molecule with two
possible structures. It is either (1) or (2). The molecule reacts with HBr to
+

give 3 and 4, then a second step, reaction with Na SH, gives 5 and 6.
Is the structure 1 or 2? Circle the correct structure, then give structures for 3,
4, 5, and 6. On the next page show arrow formalisms for their formations and
explain how you know the structure of the starting molecule (1 or 2).

??

??

HBr

3
Na +

SH

Na +

SH

5 (12 points) Compounds A and B differ only in the stereochemistry of one

methyl group. Thus, one might expect that the energy difference between them
would be about the same as that between axial and equatorial
methylcyclohexane, 1.74 kcal/mol. But, in fact, B is more stable than A by
much more than that, 3.7 kcal/mol.

First, make excellent three-dimensional drawings of A and B in their
energy-minimum forms in the boxes shown, then use those drawings to explain
why the energy difference is so great.
H3C
CH3
CH3
H3C
A, less stable

H3C
CH3
CH3
H3C
B, more stable

6 (12 points). Here are four short answers to four short questions.
Something is wrong with each answer. Tell us what is wrong in each
case. Do NOT write a book-long answer! The overly-wordy answer to all
parts uses a total of 51 words.

(a) Draw the product of the reaction of RO with CH3OH:

RO

H 3C

RO

OH

CH 3

(b) Draw the product of the reaction of HS with (R)-2-iodobutane:

HS

SH

I
H
(R)

H
(R)

OH

(c) Draw the product of the reaction of cyanide with 1-iodoadamantane:

NC
CN

(d) Draw the transition state for a generic SN2 reaction of a nucleophile,

Nu with a substrate CH3L. Tell us the hybridization of carbon in the

transition state.
H

Nu

C
H

L
H

C is sp 2