Stereochemistry and The Flow of Electrons Exam Practice

 

ORGANIC CHEMISTRY I (CHEM 2242) EXAM #5

 

NOVEMBER 24, 2020 60 POINTS

 

 

 

 

 

 

 

 

 

 

 

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)

 

1

.

(

sia

)

2

BH

2

.

H

2

O

2

,

NaOH

 

 

 

CH3 Br

CH

3

CH3CH3

 

 

 

CH

3

NaH

Br

 

 

 

 

H3C H3C

CH

3

Cl

 

 

H

3

C

HBr

(2

 

equiv.)

CH

3

 

 

 

 

CH

3

CH

3

OH

H

2

SO

4

 

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

 

 

CH

3

CH

3

H

3

C

OH

H

2

SO

4

CH

3

CH

3

CH

3

1)

2)

H

2

,

Pd

CaCO

3

 

 

 

 

 

HBr

CH

3

OH

heat

CH

3

Alkyne

 

 

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)

H2SO4

OH

 

 

 

 

 

 

 

 

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)

CH3 – CH3 Br Na+ OCH3

CH3 CH3

 

 

 

 

 

 

 

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

multiple

steps

HO

O

Br

Br

CH

3

 

 

 

 

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