Organic Chemistry I Problem Set 6 Answer Key Alkanes and Conformation

I. Write names (IUPAC or common) for the following structures:

Cl

1.

CH3 CH CH3 CH3 CH CH CH2 CH3 CH3

2.

Cl

3-ethyl-2,4-dimethylpentane
CH3

cis-1,3-dichlorocyclopentane 4. cyclopropylcyclopentane 6. bicyclo[3.1.0]hexane

3.

CH3 H

cis-1,2-dimethylcyclohexane 5.

CH3

CH CH2 CH2

1,2-dicyclohexylbutane 7.
CH3 C CH3 CH3 C CH3

8.

2,3-dimethyl-2-butene 9.

1-isopropyl-3-methylcyclopentane 10.

CH3

Cl

CH3CH2

Cl

CH3CH2

trans-1,2-dichloropropene

2-ethyl-1-butene

II.

Write structural formulas: 1. neopentane CH3 CH3 C CH3 CH3 2. isobutyl bromide CH3 CH3 CH CH2 Br

3. sec-butylcyclopentane
CH3 CH CH2 CH3 CH H2C CH2 CH2 CH2

4. trans-1,2-dichlorocyclopropane

Cl

Cl

III.

Answer these: 1. Construct an energy diagram for rotation about the C2 C3 bond axis of 2methylbutane. Write Newman projections at all maxima and minima. I
CH3 H H H CH3 CH3 H CH3 H

II
H CH3 CH3
H

III
CH3

CH3

H CH3

There are two staggered conformations and one eclipsed. Conformation III has the highest energy, I has the next highest energy, and II the least energy. The energy diagram can be constructed as outlined on p100 of the text.

2.

Write structures that clearly show the most stable conformation for each of these: 1. ethylcyclohexane H CH2CH3

2. cis-1-isopropyl-2-methylcyclohexane H H CH3 3. trans-1,4-dimethylcyclohexane IsoPro

H CH3 CH3 H

3.

An alkane of formula C6H14 is found to produce only 2 monochloro derivatives when reacted with Cl2 and light. Write the structure of this alkane. CH3 CH3 CH3 CH CH CH3

4.

Discuss the types of strain in cis-1,2-dimethylcyclopropane which cause it to contain more energy than other isomers of C5H10 . A three-membered ring has a large amount of angle strain as the normal 109.5 CC bond angles are at 60. In 3 and 4-membered rings, all substitutant groups are in the eclipsed position. The two methyl groups, both being on the same side of the ring in the cis conformation, have significant steric interference because of their bulk and close proximity.

5.

Use the letters and arrange these compounds in order of increasing boiling points. a. CH3 CH3 C CH3 CH3 CH3 CH3 CH CH2 CH3 CH3 CH3 CH CH3 b. OH CH3 CH2 CH CH3

c.

d.

e.

CH3 CH2 CH2 CH3 __d__ < _e___ < __a_ < __c__ < __b__

6.

Chlorination of alkanes is often not very useful because of the formation of multiple products. For example, write names and structures of all dichloro products formed in the chlorination of butane.
Cl

1,1-dichlorobutane 1,2-dichlorobutane 1,3-dichlorobutane 1,4-dichlorobutane 2,2-dichlorobutane

CH3 CH2 CH2 CH Cl Cl CH3 CH2 CH CH2 Cl Cl CH3 CH CH2 CH2 Cl Cl CH2 CH2 CH2 CH2 Cl Cl CH3 CH2 C CH3 Cl Cl Cl

2,3-dichlorobutane

CH3 CH CH CH3

7.

These names are incorrect. Give the correct names. 1. 2. 3. 2-ethylpentane 5-ethyl-4-methylhexane 2,3-diisopropylbutane 3-methylhexane 3,4-dimethylheptane 2,3,4,5-tetramethylhexane