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Organic Chemistry II Exam: 5 Questions | CH 332, Exams of Organic Chemistry

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

Typology: Exams

Pre 2010

Uploaded on 07/23/2009

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Name: _______________________________________
(please print)
Chemistry 332
Organic Chemistry II
Exam 1
Margined blister beetle (Epicauta pestifera)
O
CH3
CH3
O
O
O
Cantharidin
Blister beetles secrete cantharidin, a powerful vesicant (blistering agent).
pf3
pf4
pf5

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Download Organic Chemistry II Exam: 5 Questions | CH 332 and more Exams Organic Chemistry in PDF only on Docsity!

Name: _______________________________________ (please print)

Chemistry 332

Organic Chemistry II

Exam 1

Margined blister beetle ( Epicauta pestifera )

O

CH 3

CH 3

O

O

O

Cantharidin

Blister beetles secrete cantharidin, a powerful vesicant (blistering agent).

  1. Draw the major organic product in each of the following reactions. Be sure to include stereochemistry where appropriate. If no reaction is expected to occur, write "NR". (4 points each)

a) Cl

  • AlCl^3

b)

Br H 2 SO 4 ∆∆∆∆

c)

Cl

Cl

HNO 3 / H 2 SO 4

d)

CH 3

O 2 N

K 2 Cr 2 O 7 H 2 SO 4 / ∆∆∆∆

e)

O

C

O

CH 3

KOH / H 2 O / EtOH ∆∆ ∆∆

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

a)

Cl

H 2 N

b)

Cl NO 2

NO 2

OH

NO 2

NO 2

c)

NH 2

Cl Cl

Br

d)

NH 2

NO 2

O 2 N N N OCH 3

e)

Br CO 2 H

  1. (cont)

f)

CO 2 H

CO 2 H

O

O

O

g) C^ NHCH (^3)

O

CO 2 H

h)

OH O^ C

O

CH 3

i) CH 3 O

CO 2 H

CH 3 O

OH

j) C

O

Cl

C

O

H

  1. What conclusions can you draw from the p Ka values of the following compounds? (10 points)

O C CH 2 OH NO 2

O

C

CH 2 OH

CN

O

C

CH 2 OH

Cl

O

C

CH 2 OH

OH

O

C

CH 2 OH

H