Practice Exam 3-C

Chemistry S-20

You should give yourself 70 minutes for this exam.

Name:

ID Number:

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.
Chemistry S-20 1 Name:

1. Each of the following transformations can be carried out in one to three steps. Fill in the reagents
required for each step. If a step is not needed, please put an "X" through that box.

1.
a)
2.
OH

3.

1. OH
b)
OH
2.

3. O

CN

1.
c)
2.

3. (+/-)

H Br
1.
d) Br
2. H Br
(+/-)
3.
Chemistry S-20 2 Name:
2. Fill in each box with the single major organic product of the indicated transformation. Be sure to indicate
stereochemistry if it is relevant! If more than one product is possible, please provide only the single most
likely product.

1. R2BH, THF
2. H2O2, NaOH
a)
3. NaBH4, MeOH

OH
1. HIO4
b)
2. NaBH4, MeOH
OH

1. mCBPA

2. MgBr

c)
3. H+ wkup
4. CrO3

1. H2, Lindlar cat.

d) Ph Ph
2. OsO4, H2O
Chemistry S-20 4 Name:

4. You have just synthesized a new compound, and the following spectroscopic data is obtained:
• From the mass spectrum, you deduce that the molecular formula is: C6H12O2
• The infrared spectrum is:

From the infrared spectrum, circle the functional From the infrared spectrum, circle the functional
groups that are definitely present: groups that are definitely absent:

O H C O C C C C O H C O C C C C

• The proton NMR spectrum is:

Draw your best choice for the structure of this molecule in the box below.
Chemistry S-20 5 Name:

5. The following reactions illustrate the versatility of alkynes in organic synthesis. Consider the following
questions.

a) Draw a complete curved-arrow mechanism for the formation of intermediate X from the starting material
under the conditions indicated. (You need not show the mechanism of the subsequent reaction of X).

b) Draw the structure of intermediate X in the box provided.

c) For each bond formed in your mechanism, identify the donor (HOMO) and acceptor (LUMO) orbitals
involved in that curved-arrow step. You may use notations such as "!*C–C" to identify the orbitals.

HBR2 H2O2 / NaOH

O

(R = bulky alkyl group) H3C

H3C H

Intermediate X

d) One strategy for synthesizing HBR2 reagents (like the one utilized above) is shown below. Please propose a
curved arrow mechanism for this reaction.

BH3
BH
Chemistry S-20 6 Name:

6. The following reaction produces several products, of which two are shown here:

O Br
O O Br Br
R
R Br2 R
+ O
O O

Br
(as a pure enantiomer) A B
(as a pure enantiomer) (as a pure enantiomer)

a) Draw a complete curved-arrow mechanism that shows how both of these products (A and B) can be formed
from this single starting material. Each step of your mechanism should indicate stereochemistry.

b) Which of these two products is more stable? (circle one)

A or B

Explain briefly.

_
 7 Name:

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

OH

(+/-)

Desired Product

_______ / 12
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 reagents containing 4 carbons or fewer. The correct answer will
require seven or fewer steps.

Starting material:
CH3

OH

H3C
OCH3

(+/-)

Desired product