Organic Chemistry Exam

 

ORGANIC CHEMISTRY I 

 

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: Draw the most stable carbocation that has the formula C5H9+. (5 points)

QUESTION 2: Classify each of the following reactions as substitution, elimination or addition. (8 points)

 

O

O

N

N

H

F

__________________________

 

 

__________________________

HN

H

3

C

CH

3

N

CH

3

H

3

C

O

H

3

C

O

Ph

I

O

O

CH

3

O

O

H

3

C

 

Two types of reaction:

__________________________

O

N

O

CF

3

O

N

O

F

MgBr

 

__________________________ QUESTION 3: Fill in the blanks for the following reactions. (3 points per blank – 18 points)

 

OH

HS

CH

3

N

+

+

O

CH3

intermediate

H

2

SO

4

,

H

2

O

H3C

CH3

CH

3

H

Br

OH

CH3 CH3

 

 

 

QUESTION 4: Predict whether Compound M has a pKa closer to that of 1-butanol or to that of butanoic acid. Explain your reasoning. (4 points)

Compound

pKa

 

1-Butanol (C4H10O)

 

16

 

Butanoic Acid (C4H8O2)

 

4.8

 

Compound M (C4H6O2)

O

H3COH

 

QUESTION 5: This compound has three possible conjugate bases. Draw each of them. (6 points)

conjugate

base

#2

conjugate

base

#3

conjugate

base

#1

O

HO

H

Cl

H

2

N

O

 

QUESTION 6: Which position on this molecule is the most acidic? Justify your answer. (3 points)

O

H2N

O

Cl

H HO

 

 

 

QUESTION 7: Draw the conjugate acid and conjugate base in the following reaction. Which side of the equilibrium is favored? You must explain your reasoning to receive full credit. (4 points)

O O

O

O

+ ?

F3CCF3 H3CCH3 H H

 

 

 

QUESTION 8: Draw the mechanisms for the following reactions. Show all necessary arrows and intermediates. (4 points each – 12 points)

H CH3CH3

O

O

O

O

+ CH3 + CH3

O

HO

 

 

 

 

 

 

H C CH3 H-Br H3C Br CH3

3

H3CH3C

 

 

 

 

 

O

H

3

C

S

Cl

O

,

 

H

2

O

S

O

O

H3C OH

CH3H3CCH3

H3CCH3

CH3

 

 

 

 

 

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