Organic Chemistry Reactions Exam

ORGANIC CHEMISTRY I (CHEM 2242) EXAM #6

 

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. (3 points per blank)

HBr,

peroxides

 

 

Br

2

,

h

ν

CH

3

 

 

CH

3

NBS,

h

υ

 

 

OH Br

H3CH3C

 

 

CH3

HBr,

RO-OR

NBS,

h

ν

H3CBr

CH3

CH3

H3CBr

 

 

 

QUESTION 2: Fill in the blanks. (3 points per blank)

 

NH

SOCl

2

H

3

C

CH

3

H

3

C

CH

3

H

3

C

CH

3

CH

3

O

H

3

C

CH

3

CH

3

CH

3

1.

2.

CH3

 

QUESTION 3: 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 O H3C O

O

CH

3

h

ν

 

 

 

 

 

 

 

 

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)

OH H-Cl Cl

H3CCH3 H3CCH3

CH3 CH3

 

 

 

 

 

 

 

 

QUESTION 5: Propose a series of steps that convert the given starting material into the product shown. (6 points)

CH3 CH3

 

 

 

 

 

 

 

 

 

 

QUESTION 6: Propose a series of steps that convert the given starting material into the product shown.

(6 points)

OH multiple steps CH3

S

H

H3CH3C

O

 

 

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