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Organic Chemistry II Exam 2: Major Products and Mechanisms - Prof. Bernhard Vogler, Exams of Organic Chemistry

University of Alabama - HuntsvilleOrganic Chemistry
Prof. Bernhard Vogler

The questions and answers for exam 2 of organic chemistry ii (chemistry 332). The exam covers drawing major organic products, suggesting mechanisms for reactions, and identifying the most basic nitrogen atom in chloroquine.

Typology: Exams

2011/2012

Uploaded on 08/18/2012

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Name: _______________________________________
(please print)
Chemistry 332
Organic Chemistry II
Exam 2
Plasmodium falciparum
Anopheles gambiae
Since 1945, chloroquine (see problem 3) has been
used to treat malaria, an infectious disease cause by
Plasmodium falciparum. This parasitic protozoan is
spread by the Anopheles mosquito.
pf3
pf4
pf5
pf8
pf9
pfa
pfd
pfe
pff

Partial preview of the text

Download Organic Chemistry II Exam 2: Major Products and Mechanisms - Prof. Bernhard Vogler and more Exams Organic Chemistry in PDF only on Docsity!

Name: _______________________________________ (please print)

Chemistry 332

Organic Chemistry II

Exam 2

Plasmodium falciparum Anopheles gambiae

Since 1945, chloroquine (see problem 3) has been

used to treat malaria, an infectious disease cause by

Plasmodium falciparum. This parasitic protozoan is

spread by the Anopheles mosquito.

  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) O 1) NaBH^4 / CH^3 OH

  1. H 3 O+

Camphor

b)

α-Pinene

mCPBA CH 2 Cl (^2)

c)

O O

xs CH 3 NH (^2) HOAc / Δ

d) N Cl

NaOCH 3 / CH 3 OH Δ

e)

O

O O

H 2 NCH 3

NaBH 3 CN / H 2 O

  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) (^) CHO CHO

b)

O

OH

O CHO

c) S S

NO 2

d) S

O

O

e)

CH 3 O

CH 3 O

OCH 3

NOH CH 3 O

CH 3 O

OCH 3

NH 2

Mescaline

  1. (cont)

f) O (^) O

g) N N

NO 2

O

h) N

O

N

i)

O

N

j)

CHO

O

  1. Suggest reasonable mechanisms for the following transformation. (5 points)

O

CO 2 Me

O

CO 2 Me

1) LDA / THF

2) H 2 O

  1. The Hantzsch pyrrole synthesis is a modification of the Feist-Benary furan synthesis and involves reaction of an α -halo ketone with a β -keto ester and ammonia. Suggest a reasonable mechanism for this reaction (Hint: alkylation of enamine followed by cyclization). (5 points)

CO 2 Et

O

Cl

O

NH 3

N

H

CO 2 Et

  1. (cont)

f)

O

Ph 3 P CH 3 I

NaH / DMSO

CH 2

(Wittig reaction)

g)

N

HNO 3 / H 2 SO 4

N

NO 2

h) N N^ NH^2

  1. NaNH 2 / Δ
  2. H 2 O (Chichibabin reaction)

i)

O

  1. CH 3 CO 2 Et / NaOEt / EtOH
  2. H 3 O+

O O

(Claisen condensation)

j) N H

py SO 3 benzene (^) N

H

SO 3 H

  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) (^) CHO CHO

H 2 / Pd CH 3 OH

b)

O

OH

CrO 3 py O^ CHO CH 2 Cl 2

c) S S

NO 2

Ac 2 O / HNO (^3) cold

d) S

O

O

P 4 S 10 / Δ

e)

CH 3 O

CH 3 O

OCH 3

NOH CH 3 O

CH 3 O

OCH 3

NH 2

Mescaline

1) LAH / THF

2) H 2 O

  1. Circle the most basic nitrogen atom in chloroquine. Briefly explain your choice. (5 points)

N

HN

N

Cl

This N is sp^3 -hybridized and not conjugated

This N is sp^2 - hybrizided

The lone pair on this N is conjugated with the aromatic group

  1. Suggest a reasonable mechanism for the following transformation. (5 points)

CH 3 O 2 C

O

O

H H

O

O

CH 3 O 2 C

  1. NaOCH 3 / CH 3 OH

  2. H 2 O

CH 3 O 2 C

O

O

deprotonation

conjugate addition O

O

CH 3 O 2 C

H 2 O

  1. Suggest reasonable mechanisms for the following transformation. (5 points)

O

CO 2 Me

H

H O

CO 2 Me

1) LDA / THF

2) H 2 O

O

CO 2 Me

deprotonation

conjugate addition

O CO^2 Me

conjugate addition

O

CO 2 Me

O

CO 2 Me

H 2 O