Organic Chemistry I Exam 4: 6 Exercises to Solve | CH 331, Exams of Organic Chemistry

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Chemistry 331

Organic Chemistry I

Exam 4

Br

HOMO H 3 C-Br LUMO

Name ________________________________________________________________ (please print)

Br

C

H

H

H

Br

1. Arrange the following nucleophiles in order of


 
nucleophilicity: Br

• , CH 3 S - , Cl - , H 2 O, OH - (5 points)

2. Arrange the following alkyl halides in order of increasing reactivity in SN 2 reaction (5 points):

CH 3 Br (^) CH 3 C

CH 3

CH 3

Br CH 3 CH 2 CH 2 CH 2 Br^

CH 3 CH

CH 3

CH 2 Br

f)

Br H LiSH DMF

g) (^) C

CH 3

H

Cl acetone/H 2 O 80:

h) OH

SOCl 2 pyridine

i)

Br xs NH 3

j) NH 2

1 ) xs CH 3 I

2. Ag 2 O/H 2 O
3. heat

4. Indicate how you would carry out each of the following transformations. Be sure to include necessary reagents, solvents, and conditions. More than one step may be necessary. (4 points each)

a) (^) Br NH 2

b) OH Cl

c)

OH

d)

Br

e) (^) OH Br

5. Reaction of 2-bromo-3-methylbutane in refluxing ethanol gives a mixture of ethers:

CH 3 CH CH CH 3

CH 3

Br CH 3 CH CH CH 3

CH 3

OCH 2 CH 3 CH 3 CH 2 C CH 3

CH 3

OCH 2 CH 3

CH 3 CH 2 OH

Suggest a reasonable mechanism for the formation of these two products. ( points)

6. The following compounds show different rates of debromination. One reacts very fast and the other shows no reaction. Explain. (10 points)

Br

(CH 3 ) 3 C Br

Br

(CH 3 ) 3 C Br

(CH 3 ) 3 C

KI / acetone (fast)

KI / acetone No Reaction