Practice Exam 6B

8:10 — 9:20 a.m.

Name:

Section TF:

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. ____________ / 14

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

6. ____________ / 12

7. ____________ / 10

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.

O
1. NH
a)
OEt
OH 2.
O
3.

1.
b)
2.
H H
3.

1.
c) CN NH2
2.

3.

CO2Et
1.
d) O
2. CO2Et

3. (+/-)

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

a) OH 1. TsCl, pyr

2. NaN3
3. H2, Pd/C

1. LDA
b)
O O 2.
3. H+ workup

1. NH2OH, pH 5
c) NH

2. H+
O

h
d) D

_______ / 12
 3 Name:

3. Provide a complete curved-arrow mechanism for the following multistep transformation.

CCl3
N
Cl3C C N H+, HN O

OH O CCl3
NaH

_______ / 14
 4 Name:

4. Provide a complete curved-arrow mechanism for all steps of the following multistep transformation.
Identify and classify all pericyclic reactions. For example: "[4s+2s], 6 e-, thermal, cycloaddition".

O OH
O D
D H+ D D
+
D

_______ / 14
 5 Name:

5. Provide a complete curved-arrow mechanism for all steps of the following multistep enzyme-catalyzed
transformation, involved in the biosynthesis of vanillin. Structures of necessary cofactors are shown below.

O SCoA O SCoA
O SCoA
O
1. H2O CoASH O
+
2. NAD+ SCoA

OH
OH OH

H O

NH2

R NAD+

_______ / 14
 6 Name:

6. Provide a complete synthesis of the following desired product, starting from benzene. You may use any
inorganic reagents, and any organic reagents with three or fewer carbons. You do not need to show any
mechanisms. The best answer will require eight or fewer total steps.

Starting Material:

Br
N
H

Br

Desired Product

_______ / 12
 7 Name:

7. Provide a complete synthesis of the following desired product. You may use any inorganic reagents, and
any organic reagents with six or fewer carbons. You do not need to show any mechanisms. You may ignore
stereochemistry. The correct answer will require three or fewer total steps.

Starting Material:

any organic reagents

with six or fewer carbons

OH

NEt2

Desired Product

_______ / 10
Chemistry S-20 8 Name:

8. Provide a multistep synthesis for the desired product from the indicated starting material. You may use
any inorganic reagents and any organic compounds containing 6 carbons or fewer. All of the carbon atoms
from the starting material must end up in the product. The correct answer will require six or fewer steps.

Starting material:
O

OH

NH

Desired product
SCRATCH PAPER ONLY - NOTHING ON THIS SHEET WILL BE GRADED