Practice Exam 6C

Chemistry S-20

Name:

Important Notes:

1. This exam consists of 8 problems on 8 pages, plus this cover sheet, and one page for scratch work at
the end of the exam.

2. All answers must be written in the spaces provided. Do not write anything in red ink. Answers
written on the back of a page will not be graded. Anything written on the scratch page will not be graded.

3. You are allowed to use a set of molecular models for this exam.

Problem Score

1. ____________ / 12

2. ____________ / 12
Total Score:
3. ____________ / 12

4. ____________ / 14
________________ / 100
5. ____________ / 14

6. ____________ / 12

7. ____________ / 12

8. ____________ / 12
 1 Name:
1. Each of the following transformations can be carried out in three or fewer steps. Fill in the reagents
required for each step. If a step is not needed, please put an "X" through that step.

NO2 OH
1.
a)

Br 2. Br

3.

O O

NH2 1. N
b) H

2.

3.

HO HN
1.
c) O

2.

3.

O
O 1.
d) HO
HO
2.
CN
3. CN

_______ / 12
 2 Name:
2. Fill in each box with the single major organic product of the indicated transformation. Be sure to indicate
the correct stereochemistry if it is relevant!

CN 1. LDA
a)
2. CH3Br
3. H2, Pd/C

O
!
b)

1. h"
c)

2. NH2

H Me
!
d)

_______ / 12
 3 Name:

3. Provide a complete curved arrow mechanism for all steps of the following transformation. Then please
classify all pericyclic reactions. (Example: 6! e-, [4s + 2s], cycloaddition).

h" CO2Me
+ MeO2C CO2Me

CO2Me

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 4 Name:

4. The following interesting cycloaddition was observed between a nitrone and an alkene.

a) Provide a curved-arrow mechanism for this cycloaddition. You may draw your arrows on the
structures provided below.

O " O
+
Me N Me N
Ph
nitrone Ph
b) It is believed that the HOMO of the nitrone reacts with the LUMO of the alkene. Draw the
"cartoon" molecular orbitals for these reactive orbitals, and show clearly how they can react to form
the observed product. The !-bond frameworks with the atoms (C, N, and O) are provided below.

N
nitrone HOMO: C O

alkene LUMO: C C

c) Nitrones can be synthesized via the following reaction. Provide a complete curved-arrow mechanism.

O
O H+
Me OH
+ N Me N
H
H Ph Ph

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 5 Name:

5. Propose reasonable mechanisms for the following biochemical transformations. All necessary cofactors are
shown.

a)
NH3

O CoA-SH O O
H3N +
O O O SCoA

O O O
b) CO2
SCoA O SCoA

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 6 Name:

6. Provide a complete synthesis of the following desired product. You may use any inorganic reagents and
organic reagents with 4 or fewer carbon atoms. You do not need to show any mechanisms. The best
answer will require four or fewer total steps.

Starting Material:

any organic reagents

with 4 or fewer
carbon atoms

(+/–)

Desired Product

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 7 Name:

7. Provide a complete synthesis of the following desired product from. You may use any inorganic reagents
plus any organic reagents with 5 or fewer carbon atoms. You do not need to show any mechanisms. The
best answer will require seven or fewer total steps.

Starting Material:

CH2

CH2

plus any organic

reagents with 5 or
fewer carbon atoms

H
H2N

(+/–)

Desired Product

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 8 Name:

8. Provide a complete synthesis of the following desired product from the starting material shown. You may
use any inorganic reagents plus any organic reagents containing two or fewer carbon atoms. You do not
need to show any mechanisms. The best answer will require eight or fewer total steps.

Starting Material:

plus any organic

reagents with two or
fewer carbon atoms

N
H

(+/!)

Desired Product

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SCRATCH PAPER ONLY - NOTHING ON THIS SHEET WILL BE GRADED