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

Material Type: Exam; Professor: Vogler; Class: ORGANIC CHEMISTRY I; Subject: Chemistry; University: University of Alabama - Huntsville; Term: Unknown 1989;

Typology: Exams

Pre 2010

Uploaded on 07/23/2009

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Chemistry 331
Organic Chemistry I
Exam 4
Br- HOMO H3C-Br LUMO
Name ________________________________________________________________
(please print)
Br
-
C
H
H
H
Br
pf3
pf4
pf5
pf8

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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)
  1. 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

  1. Ag 2 O/H 2 O
  2. heat
  1. 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

  1. 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)

  1. 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