CHEM 237 Quiz 2B Key

Dr. Neils Andersen

Autumn 2009

Name:
Section:
TA:

1) Write structural formulas for each of the following alcohols and alkyl halides:
(4pts)
Cl

a) 2-cyclopropylethyl chloride
H
H

H
H
H
H
H

b) trans-5-tert-Butylcyclohexanol

Br

OH

OH

c) 2,5 Dibromo-3-methyl-4-octanol

CH3

Br

OH

d) Cyclopentanol
2) Exclusive of compounds with double bonds, four hydrocarbons are constitutional
isomers of cis- and trans-1,2-dimethylcyclopropane. Draw these compounds. (1pt
each)

3) Draw the two chair conformations of trans-1-chloro-2-methylcyclohexane.

Which is more stable? (4 pts)
H
H

CH3

H
H

H
H

CH3

H
H

H
H

Cl

H
Cl

More Stable

4) Rank the following (a) in terms of heats of combustion and (b) in order of
increasing stability. (3 pts)

Least Stable
Highest Heat of Combustion

5) Sight down the C2-C3 bond and draw Newman projection formulas for: (6 pts)
a) The least stable staggered conformation of 2-methylbutane
CH3
H
H3 C

CH3
CH3

H3 C

H3 C

less stable
b) The two conformations of 2,2-dimethylbutane and indicate which is less
stable
H

H CH3

CH3
H3 C

H
CH3

H3 C

CH3
H

H3C

CH3

Eclipsed, less stable

6) Name each of the following compounds: (4 pts)

a) Cl2CHCClHBr 1-Bromo-1,2,2-trichloro-ethane (1 pt)

b) (CH3)2CHCH2CH2CH2CH2Br

1-Bromo-5-Methyl-Hexane (1 pt)

CH2OH

c)

Cl

2-(1-chloroethyl) pentan-1-ol (2 pts)

7) In each of the following sets, circle the compound that has the carbon with the
highest oxidation state. (1 pt each)
a) CH3OH

or

HCO2H

b) CH2Cl2

or

CHCl3

or

CO2

8) The diaxial conformation of cis-1,3 dimethylcyclohexane is approximately 23

kJ/mol (5.4 kcal/mol) less stable than the diequatorial conformation. Draw the
two possible chair conformations and suggest a reason for the large energy
difference. (3 pts)
Less stable, 1,3 diaxial interaction
CH3

CH3

H
H3C
H

H
H

CH3

H
H

H
H

H
H