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Problem Set 5 Solution PDF

This document contains an 8 question problem set on organic chemistry concepts including: 1) Naming compounds using R,S and E,Z designations 2) Drawing Fischer projections 3) Identifying types of isomers from structures 4) Drawing products and stereoisomers from reactions 5) Drawing structures of specified compounds 6) Identifying types of isomers from Newman projections 7) Drawing chair conformers and indicating relative stability 8) Drawing most stable conformations using Newman projections

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155 views3 pages

Problem Set 5 Solution PDF

This document contains an 8 question problem set on organic chemistry concepts including: 1) Naming compounds using R,S and E,Z designations 2) Drawing Fischer projections 3) Identifying types of isomers from structures 4) Drawing products and stereoisomers from reactions 5) Drawing structures of specified compounds 6) Identifying types of isomers from Newman projections 7) Drawing chair conformers and indicating relative stability 8) Drawing most stable conformations using Newman projections

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Louis
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CHEM1280 Problem Set 5

(Due on 31 Oct. 2012)

1. Name the following compounds using R,S and E,Z designations where necessary:

(a) (S)-2,3-dimethylpentane
(b) (Z)-3-bromohex-2-ene
(c) (R)-1,3-dibromohexane
(d) (2R,3R)-2,3-dibromobutane
(e) 1-bromo-1-fluorocyclohexane

2. Draw the Fischer project for a diastereomer of following:

3. Indicate whether the following pairs of structures represent identical compounds,


enantiomers, diastereomers, or constitutional isomers:

1
4. Give the products that would be obtained from the reactions of cis-2-butene with each of
following reagents. If the products can exist as stereisomers, show which stereoisomers
are formed.
a. HCl b. H2O + H2SO4 c. H2, Pt/C

a.

b.

c.

5. Draw the structures for each of the following:


a. (S)-1-bromo-1-chlorobutane

b. two achiral stereoisomers of (3S, 5S)-3,4,5-trimethylheptane

6. Select a pair of enantiomers, a pair of conformers, and a pair of diastereomers from the
following Newman projections.

Enantiomers: (B and D) or (A and D)


Conformers: (A and B)
Diastereoisomers: (A and C) or ( B and C) or (D and C)

2
7. Draw the two chair conformers for each of the following, and indicate which conformer
is more stable:
a. cis-1-ethyl-3-methylcyclohexane

b. trans-1-ethyl-2-isopropylcyclohexane

c. trans-1-ethyl-3-methylcyclohexane

d. cis-1-ethyl-3-isopropylcyclohexane

8. Using Newman projections, draw the most stable conformation for the following:
a. 3-methylpentane, considering rotation about the C-2—C-3 bond

b. 3-methylhexane, considering rotation about the C-3—C-4 bond

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