Practice Problems for Chapter 3

1. Name the following compounds using IUPAC nomenclature.12

3

456789CH3CH2CHCH2CH2CH2C(CH3)2

CH2CH3

Br 7-bromo-3,3-dimethylnonane

CH2CH3

HCH3

H

1

23

4

5

Cis -1-ethyl-3-methylcyclopentane2. Name the functional groups in the compound at right and draw an arrow from

each functional group to its appropriate name

C

O

H2N COH

O

carbonyl group

carboxyl groupdoublebondamino

group3. Draw all nine of the constitutional (structural) isomers of C7H16 in skeletal form

1

C6 +C1

2-methylhexane 3-methylhexane

C5+C1+C1

2,3-dimethylpentane 2,4-dimethylpentane 2,2-dimethylpentane 3,3-dimethylpentane

C4+C1+C1+C1

2,2,3-trimethylbutane

C5+C2

3-ethylpentane

4. Show the general structure for each functional group below

R NH2 RC

O

O

R RC

H

O

RC

O

O

H R C NR O R

R = generic alkyl group

a) amine b) ester c) aldehyde

d) ether e) carboxylic acid f) nitrile

5. Draw all the structural isomers for alcohols with the formula C5H12O.alcohols contain the -OH functional group

HO CH2CH2CH2CH2CH3 CHCH2CH2CH3CH3

OH

CH3CH2 CHCH2CH3

OH

CCH3

CH3

CH2CH3

OH

C5+OH

C4+C1+OH

CHCH3

CH3

CHCH3

OHHO CH2CH2CHCH3

CH3

HO CH2CHCH2CH3

CH3

CH3 C

CH3

CH2-OHCH3

C3+C1+C1+OH

6. Name the following compounds using IUPAC nomenclature.

CH3CHCHCH2CHCH(CH3)2

CH3

CH2CH3

CH2CH312

34

56

78

3-ethyl-2,5,6-trimethyloctane

CH3

H

H

CH2CH3

trans-1-ethyl-3-methylcyclohexane

7. Label the carbons in the structure at right as either 1°, 2°, 3° or 4°

1˚

1˚2˚

2˚

2˚2˚

2˚

2˚

4˚

3˚3˚

8. Circle each functional group in the structure, below, and connect the circle to thename for the functional group.

ON

OO

CH2 NH CH3

CO OH

OH

C

O

OCH3

C

N

cyano group carbonyl group

double bond

amido group

amino group

carboxyl grouphydroxylgroup

oxogroup

carboxylategroup

9. Show the IUPAC name for the structure at right.

CH3CHCH2CH2CCH2CH3

CHCH3 CH3

CHCH3CH3

CH3

12

3456

78

3-ethyl-2,3,6,7-tetramethyloctane

10. Identify each carbon, in the structure at right, as 1°, 2°, 3°, or 4°.1˚

1˚

1˚

2˚

2˚

2˚

2˚2˚

3˚

4˚

11. Draw, below, all the structural isomers for bromoalkanes with the formulaC5H12Br.

Br

Br

Br

Br Br

Br Br

Br

C5+Br

C4+C1+Br

C3+C1+C1+Br