Organic Chemistry

substituent getting as low a number as possible. If two substituents have the same

low number, the ring is numbered—either clockwise or counterclockwise—in

the direction that gives the third substituent the lowest possible number. For

example, the correct name of the following compound is 4-ethyl-2-methyl-

1-propylcyclohexane, not 5-ethyl-1-methyl-2-propylcyclohexane:

PROBLEM 8

Convert the following condensed structures into skeletal structures (remember that con-

densed structures show atoms but few, if any, bonds, whereas skeletal structures show

bonds but few, if any, atoms):

a. c.

b. d.

PROBLEM 9

Give the systematic name for each of the following compounds:

a. e.

b. f.

c. g.

d. h.

CH 3 CHCH 3

CH 3 CH 2 CHCH 3

H 3 C CH 2 CH 3

H 3 C

CH 2 CHCH 3

CH 3

CH 2 CH 3 CH 2 CH 3

CH 3 CHCH 2 CH 2 CH 3

CH 3

CH 2 CH 3

CH 3 CH 2 CHCH 2 CHCH 2 CH 3 CH 3 CH 2 CH 2 CH 2 OCH 3

CH 3 CH 3

CH 3 CHCH 2 CH 2 CHCH 3

Br

CH 3

CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 OH

4-ethyl-2-methyl-1-propylcyclohexane

not

1-ethyl-3-methyl-4-propylcyclohexane

because 2 < 3

not

5-ethyl-1-methyl-2-propylcyclohexane

because 4 < 5

1,1,2-trimethylcyclopentane

not

1,2,2-trimethylcyclopentane

because 1 < 2

not

1,1,5-trimethylcyclopentane

because 2 < 5

CH 3 CH 2 CH 3

CH 3 CH 2 CH (^2) CH
3
CH 3
CH 3
72 CHAPTER 2 An Introduction to Organic Compounds
Tutorial:
Advanced alkane
nomenclature
BRUI02-060_108r4 20-03-2003 11:47 AM Page 72