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Sample Test

Essential Organic Chemistry, 2e (Bruice)

Chapter 3

 

An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure

 

1)

 

Explain what is meant by the term “saturated hydrocarbons.”

Answer:

 

These are compounds containing only single bonded carbons and hydrogens where each carbon has the maximum number of hydrogens bonded to it. The alkanes are saturated hydrocarbons.

Section:

 

3.0

 

2)

 

Describe the carbon-carbon bond differences between alkanes, alkene, and alkynes.

Answer:

 

Alkanes contain only carbon-carbon single bonds. Alkenes contain at least one carbon-carbon double bond. Alkynes contain at least one carbon-carbon triple bond.

Section:

 

3.0

 

3)

 

Explain the relationship between alkanes and gasoline.

Answer:

 

Petroleum is a complex mixture of alkanes and cycloalkanes that are separated into different fractions by distillation. 5 to 11-carbon alkanes are used for gasoline. Straight-chain alkanes  are poor fuels so catalytic cracking is used to convert these straight-chain alkanes  into branched-chain alkanes which are high-performance fuels.

Section:

 

3.0

 

4)

 

Explain why alkanes are generally considered unreactive compounds.

Answer:

 

They are unreactive because they have only strong σ bonds and atoms which have no partial charges.

Section:

 

3.0

 

5)

 

Which of the following is the best description of propane, CH3CH2CH3, at room temperature?

A)

 

liquid, soluble in H2O

B)

 

gas, soluble in gasoline

C)

 

liquid, soluble in gasoline

D)

 

gas, soluble in water

E)

 

solid, soluble in gasoline

Answer:

 

B

Section:

 

3.1

 

6)

 

The following molecule contains how many 1°, 2°, and 3° hydrogens?

 

 

Answer:

 

12 =1°, 6 =2°, 2 =3°

Section:

 

3.1

 

7)

 

Which of the following is a tertiary amine?

A)

 

 

 

B)

 

 

 

C)

 

 

 

D)

 

 

 

E)

 

 

 

Answer:

 

E

Section:

 

3.1 and 3.5

 

8)

 

There are 8 isomers that have the molecular formula C5H11Br. How many of these are tertiary alkyl bromides?

A)

 

0

B)

 

1

C)

 

2

D)

 

3

E)

 

8

Answer:

 

B

Section:

 

3.1

 

 

9)

 

Draw the structure for 3-ethyl-5-isobutyldecane.

Answer:

 

 

 

 

Section:

 

3.1

 

10)

 

Which of the following is sec-butyl alcohol?

A)

 

CH3CH2CH2CH2OH

B)

 

CH3CH(OH)CH2CH3

C)

 

(CH3)2CHCH2OH

D)

 

(CH3)2CHOH

E)

 

(CH3)2CHOCH3

Answer:

 

B

Section:

 

3.1

 

11)

 

How should (CH3)2C(OH)CH2CH3 be classified?

A)

 

primary alcohol

B)

 

secondary alcohol

C)

 

tertiary alcohol

D)

 

quarternary alcohol

E)

 

none of the above

Answer:

 

C

Section:

 

3.1 and 3.5

 

12)

 

How should CH3CHClCH2CH3 be classified?

A)

 

primary alkyl halide

B)

 

secondary alkyl halide

C)

 

tertiary alkyl halide

D)

 

quarternary alkyl halide

E)

 

pentanary alkyl halide

Answer:

 

B

Section:

 

3.1 and 3.5

 

13)

 

What is the common name for the following structure?

 

 

 

A)

 

Isobutane

B)

 

Isopropylmethane

C)

 

t-Butane

D)

 

n-Butane

E)

 

sec-Butane

Answer:

 

A

Section:

 

3.2

 

14)

 

Give the IUPAC name for the following structure:

 

A)

 

2-methyl-3-ethylheptane

B)

 

3-ethyl-2-methylheptane

C)

 

5-Isopropyloctane

D)

 

4-Isopropyloctane

E)

 

2-methyl-3-propylheptane

Answer:

 

D

Section:

 

3.2

 

15)

 

There is something wrong with the following name. Write the structure and correct the name: 2-ethylpropane.

Answer:

 

 

The correct name is 2-methylbutane.

Section:

 

3.2

 

 

16)

 

Give structures for the three isomers with molecular formula C5H12 and provide the common name of each.

Answer:

 

 

 

Section:

 

3.2

 

17)

 

Provide an acceptable name for the alkane shown below.

 

CH3CH2CH2CH2CH2CH3

Answer:

 

hexane or n-hexane

Section:

 

3.2

 

18)

 

Provide an acceptable name for the alkane shown below.

 

 

Answer:

 

2,5-dimethylheptane

Section:

 

3.2

 

19)

 

Provide an acceptable name for the alkane shown below.

 

 

Answer:

 

5-sec-butyl-2,2-dimethylnonane or

2,2-dimethyl-5-(1-methylpropyl) nonane

Section:

 

3.2

 

20)

 

Provide an acceptable name for the alkane shown below.

 

 

 

Answer:

 

4-isopropyldecane or 4-(1-methlyethyl) decane

Section:

 

3.2

 

 

21)

 

Provide an acceptable name for the alkane shown below.

 

 

Answer:

 

3-ethyl-6-methyl-5-propylnonane

Section:

 

3.2

 

22)

 

Provide an acceptable name for the alkane shown below.

 

 

Answer:

 

3-Ethyl-4, 4-dimethylheptane

Section:

 

3.2

 

23)

 

Draw an acceptable structure for 4-t-butyloctane.

Answer:

 

 

 

Section:

 

3.2

 

24)

 

Draw an acceptable structure for 3-ethyl-3-methylhexane.

Answer:

 

 

 

Section:

 

3.2

 

25)

 

Draw an acceptable structure for 4-isopropyl-2-methylheptane.

Answer:

 

 

 

Section:

 

3.2

 

 

26)

 

Draw an acceptable structure for 6-ethyl-2,6,7-trimethyl-5-propylnonane.

Answer:

 

 

 

Section:

 

3.2

 

27)

 

Provide an acceptable name for the alkane shown below.

 

 

Answer:

 

2,2,3,6-tetramethylheptane

Section:

 

3.2

 

28)

 

Provide an acceptable name for the alkane shown below.

 

 

Answer:

 

6-ethyl-2-methyl-5-propyldecane

Section:

 

3.2

 

29)

 

Give the systematic name of the alkane shown below.

 

 

Answer:

 

4-ethyl-2,2,7-trimethylnonane

Section:

 

3.2

 

 

30)

 

Give the systematic name of the alkane shown below.

 

 

Answer:

 

3-ethyl-4-isopropyloctane

Section:

 

3.2

 

31)

 

Give the systematic name of the cycloalkane shown below.

 

 

Answer:

 

4-butyl-1,2-dimethylcyclohexane

Section:

 

3.3

 

32)

 

Draw an acceptable structure for sec-butylcyclopentane.

Answer:

 

 

 

Section:

 

3.3

 

33)

 

What is the common name for the following structure?

 

 

 

A)

 

Isobutyl bromide

B)

 

t-Butyl bromide

C)

 

Neobutyl bromide

D)

 

sec-Butyl bromide

E)

 

Isopropyl methyl bromide

Answer:

 

B

Section:

 

3.4

 

 

34)

 

Give the IUPAC name for the following compound:

 

 

A)

 

1-chloro-2-methylcyclohexane

B)

 

1-methyl-2-chlorocyclohexane

C)

 

1-chloro-5-methylcyclohexane

D)

 

1-methyl-5-chlorocyclohexane

E)

 

1,2-chloromethylcyclohexane

Answer:

 

A

Section:

 

3.4

 

35)

 

Draw the structure for 3-iodo-5-isopropyl-3,4-dimethylheptane

Answer:

 

 

 

 

Section:

 

3.4

 

36)

 

Draw the structure for 2-chloro-3-ethylpentane

Answer:

 

 

 

 

Section:

 

3.4

 

37)

 

Draw the structure of 2,3-dibromo-2-methylbutane.

Answer:

 

 

 

 

Section:

 

3.4

 

 

38)

 

How is the structure shown below classified?

 

 

A)

 

a primary alkyl halide

B)

 

a primary alcohol

C)

 

a secondary alkyl halide

D)

 

a secondary alcohol

E)

 

a tertiary alkyl halide

Answer:

 

C

Section:

 

3.5

 

39)

 

How is the structure shown below classified?

 

A)

 

a quarternary ammonium ion

B)

 

a quarternary amine

C)

 

a secondary amine

D)

 

a primary amine

E)

 

a tertiary amine

Answer:

 

E

Section:

 

3.5

 

40)

 

How is (CH3)3CCHClCH3 classified?

A)

 

a primary alkyl halide

B)

 

a primary alkyl chloride

C)

 

a secondary alkyl chloride

D)

 

a tertiary alkyl chloride

E)