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Name:........................KEY..................................
(please print).
ORGANIC CHEMISTRY II
CHEMISTRY 332
Summer 2012
EXAM 3
Key:Q1: 15pts, Q2:20 points Q3: 15 points Q4: 20 points
Q5: 15 points Q6:15 points
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Org Chem II Exam 3: Pyrrole & Pyrrolidine Dipole Moments, Reactions & Lipid Classification, Exams of Organic Chemistry
The third exam for organic chemistry ii (chem 332) held during the summer 2012 semester. The exam covers topics such as the difference in dipole moments between pyrrole and pyrrolidine, the completion of various reactions including nucleophilic substitution, electrophilic aromatic substitution, and elimination reactions, and the classification of different lipids. Students are required to answer multiple-choice questions, fill in the blanks, and draw structures.
Typology: Exams
2011/2012
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Name:........................KEY..................................
(please print).
ORGANIC CHEMISTRY II
CHEMISTRY 332
Summer 2012
EXAM 3
Key:Q1: 15pts, Q2:20 points Q3: 15 points Q4: 20 points
Q5: 15 points Q6:15 points
1. Pyrrole and Pyrrolidine do have very different dipol moments.
Explain why this occurs.
N
H
N
H
S O
O
S
pyrrole pyrrolidine
N
H
N
H+
CH
N
H
resonance (^) inductive effect
a) Indicate which is Pyrrole/Pyrrolidine (3 pts)
b) indicate the direction of the dipol (use + ) to indicate the
positive /negative end of the dipol moment (5 points)
c) What contributes to the respective dipolmoment in each one
the compounds (7 pts)
Pyrrol : resonance generates pos charage at N
Pyrrolidine: difference in electronegativity polarizes bonds as
shown.
2. Complete each of the following reactions. Be sure to include
stereochemistry, where appropriate. Consider several steps,
where necessary. (5 points each). (20 points total)
a)
Br
N
CH 3
O
N
CH 3 O-^ / MeOH
nucleophilic subsitution
OH
O
H OH
HO H
H OH
H OH
OH
O
H OH
HO H
HO H
H OH
D-galactose D-glucose
O
H
H
H
HO
H
OH
H OH
OH
OH
-D-Galactopyranose
O
OHH
H
H
HO
H
HO OH
H
OH
O
OHH
H
H
HO
H
HO
HO
H
HO
-L-Galactopyranose
OH
O
H OH
HO H
HO H
H OH
HNO 3
H O
OH
O
H OH
HO H
HO H
H OH
O
Symmetry ==> not chiral,
meso
4.Provide a detailed stepwise account for the following reactions (
points each).
a) provide also the final product after repeating the 2nd sequence of
steps.
N
H
CH 3
H 3 C 1. CH 3 I excess
2. Ag 2 O
3. heat
CH 3
H 2 C
N
CH 3
CH 3
1. CH 3 I excess
2. Ag 2 O
3. heat HC
2
CH 2
CH 3
CH 3
H 3 C
N
CH 3
H 3 C
I
- H 3 C CH 3
N+^ CH 3
H 3 C
H O -
b) You may use Gabriel synthesis to construct a primary amine. Use
Phtalimide, KOH, hydrazine, and 1-bromopentane as the reagents.
What is the product? Show the course of the reaction.
O
O
NH
phtalimide
NaOH
O
O
N
BrCH 2 CH 2 CH 2 CH 2 CH 3
CH 2
O
O
N CH 2
CH 2
CH 2
CH 3
H 2 NNH 2
O
O
NH
NH
H 2 N CH
3