Organic Chemistry I Exam Paper

ORGANIC CHEMISTRY I (CHEM 2242) EXAM #4

BEFORE YOU BEGIN, TAKE A MOMENT TO WRITE DOWN HERE TWO THINGS ON THIS EXAM

THAT YOU ARE CONFIDENT THAT YOU UNDERSTAND:

 

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**TAKE A BREATH**

QUESTION 1: Fill in the blanks in the following reactions. Include stereochemistry when relevant. (4 points per blank)

 

O

1)

 

O

3

2)

 

(

CH

3

)

2

S

H + O

 

 

 

 

H

3

C

CH

3

OH

Br

CH

3

+

S

 

 

 

 

H

3

C

P

H

CH

3

H

3

C

CH

3

Br

CH

3

+

H

N

CH

3

1)

 

BH

3

*

THF

2)

 

H

2

O

2

,

NaOH

 

 

CH3

1

.

Hg(OAc)

2

,

H

2

O

2

.

NaBH

4

CH3

OH

 

 

CH3

(

CH

3

)

2

NH

 

H3CCH3

I

 

CH3

OH

 

H3CCH3

I

 

Br H2, Pt

 

1)

H3C

CH3 2) CH3CH2OH

 

 

QUESTION 2: Which of the following products cannot be made from this starting alkene? (2 points)

 

H3C

starting alkene

H3C OH OH

A)

H3C Br

B)

Br

H3C H

C)

OH

H3C OH Br

D)

 

 

 

QUESTION 3: Fill in the reagents and conditions for each step.

(3 points per step)

 

 

H3C H3C

CH3

CH3

Cl

O

 

 

 

 

 

OH

CH3

 

 

 

QUESTION 4: Draw a mechanism for the following transformation that shows the flow of electrons leading to the product. Show any intermediates in the mechanism. (6 points)

H3CH3C

Br OCH3

CH

3

OH

 

 

 

 

 

 

 

 

 

QUESTION 5: Draw a mechanism for the following transformation that shows the flow of electrons leading to the product. Show any intermediates in the mechanism.

(6 points)

H3C

H3C OH

Br2, H2OBr

 

 

 

 

 

 

 

 

 

 

 

 

QUESTION 6: Identify the leaving group and the nucleophile in the following SN2 reaction. (5 points)

 

H

N

O

O

CH

3

H3C CHN 3 3C CH3

CH

H3CH3C3

 

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