Organic Chemistry

PROBLEM 4

Draw the structure of each of the following compounds:

a. 2,3-dimethylhexane d. 2,2-dimethyl-4-propyloctane

b. 4-isopropyl-2,4,5-trimethylheptane e. 4-isobutyl-2,5-dimethyloctane

c. 4,4-diethyldecane f. 4-(1,1-dimethylethyl)octane

PROBLEM 5 SOLVED

a. Draw the 18 isomeric octanes.

b. Give each isomer its systematic name.

c. How many isomers have common names?

d. Which isomers contain an isopropyl group?

e. Which isomers contain a sec-butyl group?

f. Which isomers contain a tert-butyl group?

SOLUTION TO 5a Start with the isomer with an eight-carbon continuous chain. Then

draw isomers with a seven-carbon continuous chain plus one methyl group. Next, draw

isomers with a six-carbon continuous chain plus two methyl groups or one ethyl group.

Then draw isomers with a five-carbon continuous chain plus three methyl groups or one

methyl group and one ethyl group. Finally, draw a four-carbon continuous chain with four

methyl groups. (You will be able to tell whether you have drawn duplicate structures by

your answers to 3b because if two structures have the same systematic name, they are the

same compound.)

PROBLEM 6

Give the systematic name for each of the following compounds:

a. f.

b. g.

c. h.

d.

e.

PROBLEM 7

Draw the structure and give the systematic name of a compound with a molecular formula

that has

a. only primary and secondary hydrogens c. one tertiary hydrogen

b. only primary hydrogens d. two secondary hydrogens

C 5 H 12

CH 3 CH 2 C(CH 2 CH 3 ) 2 CH(CH 3 )CH(CH 2 CH 2 CH 3 ) 2

CH 3 CHCH 2 CH 2 CHCH 3

CH 2 CH 3

CH 3

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

CH(CH 3 ) 2

CH 3 CH 2 C(CH 2 CH 3 ) 2 CH 2 CH 2 CH 3

CH 3 C CHCH 2 CH 3

CH 2 CH 2 CH 3

CH 3 CH 2 CH 2 CH 3

CH 3 CH 2 C(CH 3 ) 3

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

CH 3 CHCH 2 CH 3

CH 3 CH 2 CHCH 2 CCH 3

CH 3

CH 3 CH 3

70 CHAPTER 2 An Introduction to Organic Compounds

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