Organic Chemistry, 6e (Smith)

Chapter 4 Alkanes

1) Which of the following statements about alkanes is not true?

A) Alkanes are aliphatic hydrocarbons.
B) Alkanes contain only C-C and C-H s bonds.
C) Alkanes are acyclic or cyclic.
D) Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number of
carbons.

2) Which of the following statements about alkanes is true?

A) Alkanes are aliphatic hydrocarbons having only C-C and C-H p bonds.
B) Cyclic alkanes have two fewer H atoms than acyclic alkanes with the same number of
carbons.
C) Acyclic alkanes contain carbons joined in one or more rings.
D) Acyclic alkanes have the general molecular formula CnH2n.

3) What is the molecular formula of an alkane that has twenty-three carbon atoms?
A) C23H46
B) C23H48
C) C23H50
D) C23H44

4) What is the molecular formula of a cycloalkane that has six carbon atoms?
A) C6H14
B) C6H10
C) C6H12
D) C6H16

5) What is the approximate C-C-C bond angle in propane?

A) 90°
B) 109.5°
C) 120°
D) 180°

6) What is the hybridization of a carbon atom in an alkane?

A) sp3
B) sp2
C) sp
D) p

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7) How many constitutional isomers are there with the molecular formula C5H12?
A) 2
B) 3
C) 4
D) 5

8) How many constitutional isomers are there with the molecular formula C6H14?
A) 2
B) 3
C) 4
D) 5

9) Which of the following is not another representation for 2-methylbutane?

A) I
B) II
C) III
D) IV

10) Which of the following compounds has primary, secondary, tertiary, and quaternary carbon
atoms?
A) Pentane
B) 2-Methylpentane
C) 2,2-Dimethylpentane
D) 2,2,3-Trimethylpentane

11) Which of the following compounds has only primary and secondary carbon atoms?
A) Pentane
B) 2-Methylpentane
C) 2,2-Dimethylpentane
D) 2,3,3-Trimethylpentane

12) Which of the following compounds has only primary, secondary, and tertiary carbon atoms?
A) Pentane
B) 2-Methylpentane
C) 2,2-Dimethylpentane
D) 2,2,3-Trimethylpentane

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13) Which of the following compounds has only primary, secondary, and quaternary carbon
atoms?
A) Pentane
B) 2-Methylpentane
C) 2,2-Dimethylpentane
D) 2,2,3-Trimethylpentane

14) Which of the following compounds has primary, secondary, and tertiary hydrogen atoms?
A) Pentane
B) Hexane
C) 2-Methylpentane
D) 2,2-Dimethylpentane

15) Which of the following compounds has only primary and secondary hydrogen atoms?
A) 2-Methylpentane
B) 2,2,3-Trimethylpentane
C) 3-Methylpentane
D) 2,2-Dimethylpentane

16) How many cycloalkane constitutional isomers (excluding stereoisomers) are there with
molecular formula C5H10?
A) 2
B) 3
C) 4
D) 5

17) What is the parent chain for the following compound?

A) Hexane
B) Heptane
C) Octane
D) Nonane

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18) What is the parent chain for the following compound?

A) Heptane
B) Octane
C) Nonane
D) Decane

19) What is the name of the alkyl group that contains two carbons in a straight chain and one-
carbon branch?
A) Ethyl
B) Propyl
C) Isopropyl
D) None of these

20) What is the IUPAC name for the following compound?

A) 4-Ethyl-5-methyloctane
B) 4-Methyl-5-ethyloctane
C) 4-Methyl-3-propylheptane
D) 4-Methyl-5-propyloctane

21) What is the IUPAC name for the following compound?

A) 3,5-Diethyl-6-methylheptane
B) 3,5-Diethyl-2-methylheptane
C) 3-Ethyl-5-isopropylheptane
D) 5-Ethyl-3-isopropylheptane

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22) What is the IUPAC name for the following compound?

A) 2,3-Dimethyl-4-sec-butylheptane
B) 4-sec-Butyl-2,3-dimethylheptane
C) 3,5,6-Trimethyl-4-propylheptane
D) 2,3,5-Trimethyl-4-propylheptane

23) What is the IUPAC name for the following compound?

A) 5-Ethyl-3,6-dimethylheptane
B) 3-Ethyl-2,5-dimethylheptane
C) 3-Ethyl-2,5-dimethyloctane
D) 5-Ethyl-3,6-dimethyloctane

24) What is the IUPAC name for the following compound?

A) 2,3,5-Trimethylhexane
B) 2,4,5-Triethylhexane
C) 2,4-Diethyl-5-methylheptane
D) 4-Ethyl-3,6-dimethyloctane

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25) What is the IUPAC name for the following compound?

A) 3-Ethyl-2,7-dimethyl-5-sec-butyldecane
B) 5-sec-Butyl-3-ethyl-2,7-dimethyldecane
C) 2,7-Dimethyl-3-ethyl-5-sec-butyldecane
D) 3-Ethyl-2,7-dimethyl-5-isobutyldecane

26) What is the IUPAC name for the following compound?

A) 3-Ethyl-1-methylcyclohexane
B) 1-Ethyl-3-methylcyclohexane
C) 1-Ethyl-3-methylhexane
D) 3-Ethyl-1-methylhexane

27) What is the IUPAC name for the following compound?

A) 1-sec-Butyl-4-isopropyl-2-methylcyclohexane
B) 1-Isopropyl-3-methyl-4-sec-butylcyclohexane
C) 4-Isopropyl-2-methyl-1-sec-butylcyclohexane
D) 1-sec-Butyl-3-isopropyl-2-methylcyclohexane

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28) What is the IUPAC name for the following compound?

A) 1,4-Dimethylcyclohexane
B) 1,3-Dimethylcyclohexane
C) 1,3-Dimethylcyclopentane
D) 1,4-Dimethylcyclopentane

29) What is the IUPAC name for the following compound?

A) 1-Butylcyclohexane
B) Cyclohexanebutane
C) 1-Cyclohexylbutane
D) Butylcyclohexane

30) What is the IUPAC name for the following compound?

A) Hexylcyclopentane
B) 1-Hexylcyclopentane
C) 1-Cyclopentylhexane
D) 1-Cyclopentylheptane

31) What is the IUPAC name for the following compound?

A) 1-Butyl-3-methylcyclohexane
B) 1-sec-Butyl-3-methylcyclohexane
C) 1-Methyl-3-sec-butylcyclohexane
D) 1-sec-Butyl-3-methylhexane

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32) What is the common name of the following alkyl group?

A) Isobutyl
B) sec-Butyl
C) Isopropyl
D) tert-Butyl

33) What is the common name of the following alkyl group?

A) Isopropyl
B) Isobutyl
C) sec-Butyl
D) tert-Butyl

34) Rank the following alkanes in order of decreasing boiling point, putting the alkane with the
highest boiling point first.

A) I > II > III

B) I > III > II
C) II > III > I
D) III > II > I

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35) Rank the following alkanes in order of increasing melting point, putting the alkane with the
lowest melting point first.

A) I < III < II

B) I < II < III
C) II < III < I
D) III < II < I

36) Which of the following statements about the conformations of acyclic alkanes is true?
A) Conformations are the same arrangements of atoms that cannot be interconverted by rotation
about single bonds.
B) In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond angle on
the adjacent carbon.
C) In the staggered conformation, the C-H bonds on one carbon are directly aligned with the C-H
bonds on the adjacent carbon.
D) Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a staggered
conformation, and vice versa.

37) Which of the following statements about the conformations of acyclic alkanes is not true?
A) The staggered and eclipsed conformations are equally stable.
B) The staggered conformations are more stable than the eclipsed conformations.
C) An energy minimum and maximum occur every 60° as the conformation changes from
staggered to eclipsed.
D) Conformations that are neither staggered nor eclipsed are intermediate in energy.

38) Which of the following statements about the conformations of acyclic alkanes is true?
A) A staggered conformation with two larger groups 180° from each other is called gauche.
B) Staggered conformations are at energy maxima and eclipsed conformations are energy
minima.
C) A staggered conformation with two larger groups 60° from each other is called anti.
D) Gauche conformations are generally higher in energy than anti conformations.

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39) Which of the following is not a conformer of butane?

A) I
B) II
C) III
D) IV

40) Which of the following are gauche conformers?

A) I and II
B) I and III
C) II and IV
D) II and III

41) Which of the following are anti conformers?

A) I and II
B) II and III
C) I and IV
D) II and IV

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42) Which of the following conformers has the highest energy?

A) I
B) II
C) III
D) IV

43) Rank the conformers of butane in order of decreasing stability, putting the most stable first.

A) IV > I > II > III

B) IV > I > III > II
C) II > III > I > IV
D) I > IV > II > III

44) Which of the following is the highest energy conformer of 2,3-dimethylbutane?

A) I
B) II
C) III
D) IV

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45) Which of the following is the lowest energy conformer of 2,3-dimethybutane?

A) I
B) II
C) III
D) IV

46) Which of the following cycloalkanes has the most angle strain?
A) Cyclopropane
B) Cyclobutane
C) Cyclopentane
D) Cyclohexane

47) Which of the following cycloalkanes has the least angle strain?
A) Cyclopropane
B) Cyclohexane
C) Cyclopentane
D) Cycloheptane

48) Which of the following chair conformations represents trans-1,3-dimethylcyclohexane?

A) I
B) II
C) III
D) IV

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49) Which of the following chair conformations represents trans-1,4-dimethylcyclohexane?

A) I
B) II
C) III
D) IV

50) Which of the following is the most stable conformation of cis-1-ethyl-3-

isopropylcyclohexane?

A) I
B) II
C) III
D) IV

51) Which of the following is the most stable conformation of trans-1-isopropyl-3-

methylcyclohexane?

A) I
B) II
C) III
D) IV

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52) Select the most stable conformer of cis-1,3-cyclohexanediol.

A) I
B) II
C) III
D) IV

53) What is the alternate chair conformation of the following compound?

A) I
B) II
C) III
D) IV

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54) Which of the following is the most stable conformation of the following compound?

A) I
B) II
C) III
D) IV

55) Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability, putting

the most stable first.

A) I > II > III > IV

B) III > II > IV > I
C) III > IV > II > I
D) I > II > IV > III

56) What are the products of the combustion of alkanes?

A) Carbon and hydrogen
B) Carbon and water
C) Carbon dioxide and hydrogen
D) Carbon dioxide and water

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57) What is the IUPAC name of the following compound?

A) Pentane
B) 2-Methylpentane
C) 2-Methyl-3-ethylpentane
D) 3-Ethyl-2-methylpentane

58) Rank the following alkanes in order of increasing boiling point.

A) I > II > III > IV

B) IV > III > II > I
C) II > III > IV > I
D) IV > III > I > II

59) Which of the following conformation is highest in energy?

A) I
B) II
C) III
D) IV

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60) What is the relation between the following pair of compounds?

A) Constitutional isomers
B) Stereoisomers
C) Identical molecules
D) Not isomers of each other

61) Which formula represents a cycloalkane with 6 carbons?

A) C6H12
B) C6H14
C) C6H16
D) C6H18

62) Which formula represents a cycloalkane with 5 carbons?

A) C5H8
B) C5H10
C) C5H12
D) C5H14

63) What is the IUPAC name for the following alkane?

A) 2,5,6,7-tetramethyloctane
B) 2,3,4,7-tetramethyloctane
C) 2,5,6,7-tetramethylheptane
D) 2,3,4,7-tetramethylheptane

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64) What is the IUPAC name for the following alkane?

A) 3-isopropyl-6-methyloctane
B) 3-isopropyl-3.7-methyloctane
C) 3-ethyl-2,6-dimethyloctane
D) 6-ethyl-3,7-dimethyloctane

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