NAME __________________________

FINAL EXAMINATION

CHEMISTRY 241-001

December 13, 2013

Please put your name on all 10 pages of the examination.

Be certain that you have both questions.

Question Score

II

Total

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 NAME __________________________

I. (70 points)

A. (3 points) Using the arrow formalism, draw the most important resonance structures.

OCH3

H Br

B. (3 points) Write a reaction that would result in the formation of a carbanion or organometallic.

C. (3 points) Show one way to generate a carbene or a carbenoid intermediate.

D. (5 points) Draw a detailed, stepwise mechanism for the following transformation.

OCH3 O
H 3O+
+ CH 3OH

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 NAME __________________________

E. (6 points) Propose a detailed, stepwise mechanism for the following transformation. Label each
individual step with appropriate designations/descriptors.

Cl
h CCl 3
+ CCl4

F. (10 points) The following reaction provides a single major product. Indicate what this product
is, and very briefly show or describe your rationale with a detailed mechanism. Is the product
chiral or achiral? If it is chiral, is it racemic or enantiomerically pure?

NaOH
Br Br ?
heat

optically pure

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 NAME __________________________

G. (3 points) Provide an example of an oxidation reaction that generates a meso compound.

H. (3 points) Show a reduction reaction that affords two optically pure diastereomers by creating
one new stereocenter.

I. (5 points) Write a detailed, stepwise mechanism to rationalize the following result.

O 1. 2 equiv NaOH O
Br HO
OH OH
H 2. H 3O+ H
enantiomerically enantiomerically
pure pure

J. (9 points) For the hypothetical exothermic reaction below, Y is the kinetic product of the
reaction and Z is the thermodynamic product (there are no intermediates). Draw the energy
versus reaction coordinate for this reaction, with the path to Y a solid line and that to Z a dashed
line. Carefully label the energies of activation, the transition states, and the free energies for the
transformation.
X Y + Z

Energy

Reaction progress

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 NAME __________________________

K. (8 points) Using the arrow formalism, draw a detailed, stepwise mechanism for a reaction that
proceeds with first order kinetics and involves a 1,2-alkyl shift.

L. (12 points) Very briefly show in equations and/or very clearly explain the differences in
reactivity between Grignard reagents and organocuprates with epoxides, ketones, alkyl halides,
esters, acyl halides and aryl halides.

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 M+

NAME __________________________

II. (30 points) For clarity in the following NMR spectra, the integration of the peaks has been indicated, along
with the coupling.

A. Provided below are the mass spectrum, IR, and 1H NMR of an unknown compound.

What is the molecular formula of this compound?

How many degrees of unsaturation are there for this compound?
Draw the structure of this compound and circle it.
Label the protons on your structure. Then assign and label the NMR peaks with the appropriate
letters.
Example of how to label protons:
CH3 -CH2 -OH

a b c

Label two (2) IR absorption peaks on the IR spectrum that are characteristic of specific bond types in the
molecule, and clearly indicate the types of bonds to which these absorptions are linked.

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 Triplet
2H
Triplet
NAMEof __________________________
J = 7 Hz
doublets
2H
Doublet J = 6 Hz,
of triplets 7 Hz
1H Doublet
J = 10 Hz, 1H
6 Hz J = 10 Hz

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 M+
NAME __________________________

B. Provided below are the mass spectrum, IR, and 1H NMR and IR of an unknown compound.

What is the molecular formula for this compound?

How many degrees of unsaturation are there for this compound?
Draw the structure of this compound and circle it.
Label the protons on your structure with letters. Then assign and label the NMR peaks with the
appropriate letters.
Label two (2) IR absorption peaks on the IR spectrum that are characteristic of specific bond types in the
molecule, and clearly indicate the types of bonds to which these absorptions are linked.

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 Singlet
6H
NAME __________________________

Doublet Doublet
2H 2H
Singlet
1H

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