CHEM 2411 Organic Chemistry I

Chapter 3: Additional Problems

1) (McMurry 3.12) Give IUPAC names for the following compounds:

a. The 3 isomers of C5H12. b.

n-pentane 3,4-dimethylhexane
isopentane (2-methylbutane)
neopentane (2,2-dimethylpropane)

c. d.

2,4-dimethylpentane 2,2,5-trimethylheptane

2) (McMurry 3.13) Draw structures corresponding to the following IUPAC

name:

a. 3,4-Dimethylnonane
b. 3-Ethyl-4,4-dimethylheptane
c. 2,2-Dimethyl-4-propyloctane d. 2,2,4-Trimethylpentane

3) (McMurray 3.16) Give IUPAC names for the following cycloalkanes:

a. b.

1,4-dimethylcyclohexane 1-methyl-3-
propylcyclopentane

c. d.

Br

3-cyclobutylpentane 1-bromo-4-ethylcyclodecane

e. f.

Br

1-isopropyl-2-methylcyclohexan 4-bromo-1-tert-butyl-2-
methylcycloheptane
4) (McMurray 3.17) Draw structures corresponding to the following IUPAC
names:

a. 1,1-Dimethylcyclooctane b. 3-Cyclobutylhexane

c. 1,2-Dichlorocyclopentane d. 1,3-Dibromo-5-
methylcyclohexane

Cl Br
Cl

Br

5) (McMurry 3.18) Name the following substances, specifying each as cis or

trans:

a. b.
CH3 H3C
H H H
Cl
CH3
H
Trans-1-chloro-4-methylcyclohexane cis-1-ethyl-3-
methylcycloheptane
6) (McMurry 3.19) Draw the structures of the following molecules:
a) trans-1-Bromo-3-methylcyclohexane

Br
H H

b) cis-1,2-Dimethylcyclopentane
H
CH3

CH3
H
c) trans-1-tert-Butyl-2-ethylcyclohexane

H
7) (McMurry 3.29) Draw as many compounds as you can that fit the following
descriptions:
a) Alcohols with formula C4H10O

OH
OH
b) Amines with formula C5H13N
 NH2
NH2 N
NH2 H

H
N N N

c) Ketones with formula C5H10O

O O
d) Aldehydes with formula C5H10O
H H H H
O O O O

e) Esters with formula C4H8O2

O O

O O

f) Ethers with formula C4H10O

O O
O

8) (McMurry 3.34) Draw structures for the following:

a) 2-Methylheptane
b) 4-Ethyl-2,2-dimethylhexane

c) 4-Ethyl-3,4-dimethyloctane

d) 2,4,4-Trimethylheptane

e) 3,3-Diethyl-2,5-dimethylnonane

f) 4-Isopropyl-3-methylheptane
9) (McMurry 3.40) Give IUPAC names for the following compounds:

a. b.

2-methylpentane 2,2-dimethylbutane

c. d.

2,3,3-trimethylhexane 5-ethyl-2-methylheptane

e. f.

3,3,5-trimethyloctane 2,2,3,3-tetramethylhexane

g.
5-ethyl-3,5-dimethyloctane

10) (McMurry 3.42) Explain why each of the following names is incorrect:

The best way to answer these questions is to draw the structure as named,
to see why it is incorrect

a) 2,2-Dimethyl-6-ethylheptane

2,2,6-trimethyloctane

b) 4-Ethyl-5,5-dimethylpentane

3-ethyl-2-methylhexane

c) 3-Ethyl-4,4-dimethylhexane
4-ethyl-2,2-dimethylhexane

d) 5,5,6-Trimethyloctane

3,4,4-trimethyloctane

e) 2-Isopropyl-4-methylheptane

2,3,5-trimethyloctane

f) cis-1,5-Dimethylcyclohexane

H3C CH3
H H

cis-1,3-dimethylcyclohexane
11) (McMurry 3.44) Give IUPAC names for the following compounds:

a. H3C b. c. CH3
H3C
H CH3 H
H CH3
H

d. e.
H3C
CH3
CH3 CH3

CH3 H3C
a. methylcycloheptane
b. cis-1,3-dimethylcyclopentane
c. trans-1,2-dimethylcyclohexane
d. trans-1-isopropyl-2-methylcyclobutane
e. 1,1,4-trimethylcyclohexane

12) (McMurry 4.27) Construct a qualitative potential-energy diagram for

rotation about the C-C bond of 1,2-dibromoethane. Which conformation
would you expect to be more stable? Label the anti and gauche
conformations of 1,2-dibromoethane.
13) (McMurry 4.31) Draw the most stable conformation of 1,4-
dichlorobutane, using wedges and dashes to represent bonds coming out of
the paper and going behind the paper, respectively.

14) (McMurry 4.32) Draw a chair cyclohexane ring and label all positions as
axial or equatorial.

15) (McMurry 4.33) Why is a 1,3-cis disubstituted cyclohexane more stable

than its trans isomer?

16) (McMurry 4.35) Which is more stable, a 1,4-trans disubstituted

cyclohexane or its cis isomer?