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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

Uploaded on 08/18/2012

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P a g e | 1
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
pf3
pf4
pf5

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Download Org Chem II Exam 3: Pyrrole & Pyrrolidine Dipole Moments, Reactions & Lipid Classification and more Exams Organic Chemistry in PDF only on Docsity!

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

Aminopentane

6. Match the following lipids with the appropriate compound

classification

(wax, fatty acid, sesquiterpene, triterpene, carotenoid, phospholipid,

monoterpene, prostaglandin, diterpene, triglyceride, steroid) (

points).

a) CH 3 (CH 2 ) 14 COO(CH 2 ) 33 CH 3 WAX

b) STEROID

c) TRIGLYCERIDE

d) DITERPENE

e)

CAROTENOID