Fourth Weekly Examination

Chemistry S-20

July 21, 2014

8:10 — 9:20 a.m.

Name:
circle
Section TF: one: Christina Esty Kaleb Peter Rahul

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.

O
1.
a)
2.

NO2
3.

1.
NH2
b)
2.

3.

1.
Br O
c)
2.
NO2

3.

1. O

d)
2.

(+/–)
3.

_______ / 12
 2 Name:
2. Fill in each box with the single major organic product of the indicated transformation. For full credit, all
reagents must be used in a meaningful way.

1. H
N
Me OMe
a) Cl
2. LiAlH4
O 3. H+ workup

OH

1. CrO3
b)
2.
N
H ,
pH 5

1. Mg, Et2O
O O 2. CO2
3. H+ workup
c)
4. H3O+

Br

1. Ph3P—CH2
O 2. OsO4 , H2O
d)
3. O

, H+

_______ / 12
 3 Name:
3. Fill in each box with the starting material of the indicated transformation. For full credit, all reagents must
be used in a meaningful way.

O
1. NaCN
a)
OH
2. H3O+, heat

OH

1. EtOH, H+
b)
2. PhMgBr
3. H+ workup

1. mCPBA
H
c)
2. DIBAL-H, –78°
3. H+ workup

1.
OH
HO , H+ OH
d)
O
2. LiAlH4
3. H3O+
H

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 4 Name:

4. Consider the three oxygen-containing rings shown below.

a) For each of the following molecules, determine if it is aromatic, anti-aromatic, or non-aromatic. Circle the
appropriate label.

O O
O

furan pyran oxepin

a) aromatic a) aromatic a) aromatic

b) antiaromatic b) antiaromatic b) antiaromatic

c) nonaromatic c) nonaromatic c) nonaromatic

b) Furan reacts with bromine to yield the following product. Draw a curved-arrow mechanism.

O Br2 O
Br

(1 equiv.)

c) Predict the product of the reaction of pyran with bromine. No mechanism is needed.

O Br2

(1 equiv.)

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 5 Name:

5. Provide a complete curved-arrow mechanism for all steps in the following multi-step transformation.

O N
1. SOCl2 2. ZnBr 3. NH2
OH
pH 5

_______ / 14
 6 Name:

6. Provide a complete curved-arrow mechanism for the following transformation. (Hint: Recall that phenol
has a pKa of 10.)

OH

OH
NO2

+ 1. NaOH

Cl 2. H+ workup NO2

_______ / 12
 7 Name:

7. Provide a complete synthesis of the following desired product from the indicated starting material. You
may use any additional inorganic or organic reagents, but all carbons from the starting material must end up in
the product. You do not need to show any mechanisms. The best answer will require five or fewer total steps.

Starting Material:

OH

Desired Product

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 8 Name:

8. Provide a complete synthesis of the following desired product starting from benzene. You may use any
additional inorganic or organic reagents, but all carbons from the starting material must end up in the product.
You do not need to show any mechanisms. The best answer will require seven or fewer total steps.

Starting Material:

OH

Desired Product

_______ / 12
SCRATCH PAPER ONLY - NOTHING ON THIS SHEET WILL BE GRADED