Chapter 4

Chapter 4

MULTIPLE CHOICE QUESTIONS Solomons Chapter 4

(Answers on pages 21-22) Uppgifter markerade * r verkurs
Topic: Nomenclature 1.

Topic: Nomenclature 5. A) B) C) D) E) Which of the following pairs of compounds represent pairs of constitutional isomers? 2-Methylbutane and pentane 2-Chlorohexane and 3-chlorohexane sec-Butyl bromide and tert-butyl bromide Propyl chloride and isopropyl chloride All of the above

A) B) C) D) E) 2.

The IUPAC name for 6-Ethyl-3,4-dimethylheptane 2-Ethyl-4,5-dimethylheptane 3,4,6-Trimethyloctane 3,5,6-Trimethyloctane 2-(1-Methylpropyl)-4-methylhexane

is:

6. Which of the following is bicyclo[3.2.2]nonane*?

II

III

A) B) C) D) E)

An IUPAC name for 5-Methyl-4-(1-methylpropyl)hexane 2-Methyl-3-(1-methylpropyl)hexane 2-Methyl-3-(2-methylpropyl)hexane 3-Methyl-4-(1-methylethyl)heptane 5-Methyl-4-(1-methylethyl)heptane

is: A) B) C) D) E) I II III IV V
IV V

3. A correct IUPAC name for the following compound is:

7. Select the systematic name for

Cl H H Cl

A) B) C) D) E)

2,5-Dimethyl-3-propylheptane 3,6-Dimethyl-5-propylheptane 6-Methyl-4-(1-methylethyl)octane 2-Methyl-3-(2-methylbutyl)hexane 3-Methyl-5-(1-methylethyl)octane

A) B) C) D) E) 9. A) B) C) D) E)

cis-1,3-Dichlorocyclopentane trans-1,4-Dichlorocyclopentane cis-1,2-Dichlorocyclopentane trans-1,3-Dichlorocyclopentane 1,1-Dichlorocyclopentane Which isomer of C5H10 would you expect to have the smallest heat of combustion*? Cyclopentane Methylcyclobutane 1,1-Dimethylcyclopropane cis-1,2-Dimethylcyclopropane trans-1,2-Dimethylcyclopropane

4. A correct IUPAC name for the following compound is:

OH

Cl

A) B) C) D) E)

4-propyl-5-chloro-3-heptanol 4-propyl-3-chloro-5-heptanol 4-(1-chloropropyl)-3-heptanol 5-chloro-4-propyl-3-heptanol 3-hydroxy-4-propyl-5-chloroheptane 87

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Topic: Nomenclature 12. What is the common name for this compound?
Br

20. cis-1,3-Dibromocyclohexane is represented by structure(s):

H Br H H Br Br Br H H Br H

Br

A) B) C) D) E)

Isobutyl bromide tert-Butyl bromide Butyl bromide sec-Butyl bromide Bromo-sec-butane

13. A correct IUPAC name for the following compound is:

Br

A) B) C) D) E) 21. A) B) C) D) E) 22. A) B) C) D) E) 23.

I II III II and III I and II

II

III

A) B) C) D)

3,6,7-trimethyl-4-bromo-1-octene 4-bromo-3-methyl-6-isopropyl-1-heptene 4-bromo-3,6,7-trimethyl-1-octene 4-bromo-6-isopropyl-3-methyl-1-heptene

An IUPAC name for the group Isopentyl Isoamyl sec-Butylmethyl 2-Methylbutyl 2-Ethylpropyl

CH3CHCH2! CH2CH3 is:

Use the following to answer questions 18-19:

Br Br H H Br H H Br Br H Br H

The neopentyl group has the alternative name: 1,1-Dimethylpropyl 1,2-Dimethylpropyl 2,2-Dimethylpropyl 1-Methylbutyl 2-Methylbutyl
Br Cl is: The correct IUPAC name for 2-Bromo-4-chloro-4-isopropylpentane 4-Bromo-2-chloro-2-isopropylpentane 5-Bromo-3-chloro-2,3-dimethylhexane 2-Bromo-4-chloro-4,5-dimethylhexane 2-(2-Bromopropyl)-2-chloro-3-methylbutane

II

III

18. A) B) C) D) E) 19. A) B) C) D) E)

trans-1,2-Dibromocyclohexane is represented by structure(s): I II III II and III I and II cis-1,2-Dibromocyclohexane is represented by structure(s): I II III II and III I and II

A) B) C) D) E)

24. Which of the following is a correct name which corresponds to the common name tertpentyl alcohol*? A) 2,2-Dimethyl-1-propanol B) 2-Ethyl-2-propanol C) 2-Methyl-2-butanol D) 3-Methyl-1-butanol E) Methyl tert-butanol Topic: Nomenclature

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25. The correct IUPAC name for the following compound is:
OH

31. Neglecting stereochemistry, which of these common group names is ambiguous, i.e., does not refer to one specific group*? A) Butyl B) sec-Butyl C) tert-Pentyl D) Neopentyl E) sec-Pentyl 32. What is the correct IUPAC name for the following compound?
OH

A) B) C) D) E)

1-Hydroxy-3-sec-butylcyclopentane 3-sec-Butyl-1-cyclopentanol 1-sec-Butyl-3-cyclopentanol 4-sec-Butyl-1-cyclopentanol 3-Isobutyl-1-cyclopentanol

26. What is a correct name for the following compound?

A) B) C) D) E)

5-Ethyl-3-methylhexanol 5-Ethyl-3-methyl-1-hexanol 2-Ethyl-4-methyl-6-hexanol 3,5-Dimethyl-7-heptanol 3,5-Dimethyl-1-heptanol

A) B) C) D) E)

3-Isobutyl-2-methylheptane 3-sec-Butyl-2-methyloctane 5-Isobutyl-6-methylheptane 2-Ethyl-3-isopropyloctane 4-Isopropyl-3-methylnonane

33. Isopentyl is the common name for which alkyl group? A) CH3CH2CH2CH
CH3 B) CH3CH2CHCH2

CH3 C) CH3CHCH2CH2
CH3 D) CH3CH2CH

28. What is the correct IUPAC name for the following compound?
HO

A) B) C) D) E) 30. A) B) C) D) E)

3-Hydroxymethylheptane 3-Hydroxymethylhexane 3-Methyloxyheptane 2-Ethyl-1-hexanol 2-Ethyl-1-heptanol Which of these is the common name for the 1,1-dimethylpropyl group*? tert-Butyl tert-Pentyl Isopentyl Neopentyl sec-Pentyl

E)

CH3 CH3

CH2CH3

CH3CCH2

34.

A) B) C) D) E)

An IUPAC name for 3-Isobutyl-2,4-dimethylhexane 3-sec-Butyl-2,5-dimethylhexane 4-sec-Butyl-2,5-dimethylhexane 4-Isopropyl-2,5-dimethylheptane 4-Isopropyl-3,6-dimethylheptane

is:

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35. An IUPAC name for the following compound is:

Topic: Conformational Analysis 40. The least stable conformation of butane is:
H H3C H H H H H H H CH3 CH3 H H3C H H CH3 H

A) B) C) D) E)

4-Isobutyl-3,4-dimethylheptane 4-sec-Butyl-2,4-dimethylheptane 2,4,5-Trimethyl-4-propylheptane 3,4,6-Trimethyl-4-propylheptane 4-Isobutyl-4,5-dimethylheptane

H3C

I
H H H H CH3 CH3

II
CH3 H H H CH3 H

III

36. What is the correct IUPAC name for the following compound?

HO

A) B) C) D) E)

3-Hydroxymethyl-2-heptene 2-(1-methylethyl)-4-hexen-1-ol 5-(1-methylethyl)-2-hexen-6-ol 5-isopropyl-2,6-hexenol 2-(1-methylethyl)-4-hepten-1-ol

OH F

A) B) C) D) E) 41. A) B) C) D) E)

I II III IV V

IV

37. What is the correct IUPAC name for the following compound?

A) B) C) D) E)

5-Ethyl-3-fluorohexanol 5-Ethyl-3-fluoro-1-hexanol 2-Ethyl-4-fluoro-6-hexanol 3-fluoro-5-methyl-7-heptanol 3-fluoro-5-methyl-1-heptanol

The preferred conformation of cis-3-tert-butyl-1-methylcyclohexane is the one in which: the tert-butyl group is axial and the methyl group is equatorial. the methyl group is axial and the tert-butyl group is equatorial. both groups are axial. both groups are equatorial. the molecule exists in a boat conformation.
CH3 H3C H H H3C H

42. What structure represents the most stable conformation of cis-1,3-dimethylcyclohexane?

H CH3 H CH3 CH3 H

38. A correct name for the following compound is:

Cl

I
H CH3 H

II
H H3C H

III
CH3

A) B) C) D) E)

3-chloro-8-methylbicyclo[4.3.0]nonane 8-Methyl-3-chlorobicyclo[4.3.1]nonane 3-Methyl-7-chlorobicyclo[4.3.0]nonane 3-Methyl-7-chlorobicyclo[4.3.1]decane 3-chloro-8-methyl[4.3.0]bicyclononane A) B) C) D) E) I II III IV V

H3C

IV

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Topic: Ring Strain 41-47 43. Which cycloalkane has the largest heat of combustion per CH2 group*?

II

III

46. A) B) C) D) E) 47. A) B) C) D) E)

Which is the most stable conformation of cyclohexane? Chair Twist Boat One-half chair Staggered Which cycloalkane has the greatest ring strain? Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane

IV

A) B) C) D) E)

I II III IV V

Topic: Conformational Analysis 48. The most stable conformation of butane is:
H H3C H 3C H H H H H H H CH3 CH3 H H H 3C H CH3 H H H H H CH3 CH3 H H H CH3 CH3 H

44. Which cycloalkane has the lowest heat of combustion per CH2 group*?

II

III

IV

A) B) C) D) E)

I II III IV V

II

III

IV

A) B) C) D) E) 45. A) B) C) D) E)

I II III IV V Which isomer would have the largest heat of combustion*? Propylcyclopropane Ethylcyclobutane Methylcyclopentane Cyclohexane Since they are all isomers, all would have the same heat of combustion.

49. The most stable conformation of 1,2-dibromoethane is:

H Br Br H H H H H H H Br Br H H Br H Br H H H H H Br Br H H H Br Br H

A) B) C) D) E)

I II III IV V

II

III

IV

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50. The most stable conformation of 2,3-dibromobutane, viewed through the C-2C-3 bond :
CH3 Br Br CH3 H H H3C H3C H H Br Br H H3C Br H Br

52. The most stable conformation of 3-bromo-2-methylpentane, viewed through the C-2C-3 bond (i.e., C-2 in the front, C-3 in the back):
H H CH3 CH3 H H3C Br H CH3 CH2CH3 H H H Br CH3 CH(CH3)2

CH3

Br CH3

I
Br H3C H3C Br H H

II
Br H H3C CH3 Br

III

I
CH3 Br
H

II
CH3 CH2CH3 CH3 Br H H

III

H H

CH3 CH2CH3

IV

IV

A) B) C) D) E)

I II III IV V

A) B) C) D) E)

I II III IV V

51. The most stable conformation of 3-bromo-2-methylpentane, viewed through the C-3C-4 bond (i.e., C-3 in the front, C-4 in the back):
CH3 Br H H H CH(CH3)2 H H Br H CH3 CH(CH3)2 H H H Br CH3 CH(CH3)2

53. The most stable conformation of 2,3-dimethylpentane, viewed through the C-2C-3 bond (i.e., C-2 in the front, C-3 in the back):
CH3 H H CH3 CH3 CH2CH3 H H3C CH3 H CH2CH3 H CH3 H H CH3 H CH(CH3)2

I
H Br H H

II
CH3 CH(CH3)2 CH3 Br H H

III

I
CH3 H CH3 H CH3

II
H3C H CH3 H

III

CH3 CH2CH3

H3CH2C

A) B) C) D) E)

I II III IV V

IV

CH3 CH(CH3)2

IV

A) B) C) D) E)

I II III IV V

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Topic: Ring Strain 54. A) B) C) D) E) Which cycloalkane has the least ring strain? Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane

59. The most stable conformation for 1,2-ethanediol (ethylene glycol) is shown below. It is the most stable conformation because:
H H H H OH OH

Topic: Conformational Analysis 55. The most stable conformation of cis-1-tert-butyl-2-methylcyclohexane is the one in which: A) the tert-butyl group is axial and the methyl group is equatorial. B) the methyl group is axial and the tert-butyl group is equatorial. C) both groups are axial. D) both groups are equatorial. E) the twist boat conformation is adopted. 56. The most stable conformation of trans-1-tert-butyl-2-methylcyclohexane is the one in which: A) the tert-butyl group is axial and the methyl group is equatorial. B) the methyl group is axial and the tert-butyl group is equatorial. C) both groups are axial. D) both groups are equatorial. E) the molecule is in the half chair conformation. 57. The most stable conformation of trans-1-tert-butyl-3-methylcyclohexane is the one in which: A) the tert-butyl group is axial and the methyl group is equatorial. B) the methyl group is axial and the tert-butyl group is equatorial. C) both groups are axial. D) both groups are equatorial. E) the twist boat conformation is adopted. 58. A) B) C) D) E) In the most stable conformation of cis-1,4-dimethylcyclohexane, the methyl groups are: one axial, one equatorial. both axial. both equatorial. alternating between being both axial and both equatorial. None of the above

A) B) C) D) E)

this corresponds to an anti conformation. in general, gauche conformations possess the minimum energy. it is stabilized by intramolecular hydrogen bonding. it is a staggered conformation. it has the highest energy of all the possibilities.

60. The graph below is a plot of the relative energies of the various conformations of:
Relative energy
0o 60o 120o 180o 240o 300o 360o

Angle of rotation

A) B) C) D) E)

Ethane Propane Chloroethane 1-Chloropropane (C1-C2 rotation) Butane (C1-C2 rotation)

61. The graph below is a plot of the relative energies of the various conformations of:
Relative energy
0o 60o 120o 180o 240o 300o 360o

Angle of rotation

A) B) C) D) E)

2-chloropropane 1,3-dichloropropane 2-methylpropane Butane (C1-C2 rotation) Butane (C2-C3 rotation) Ans: E 100

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Topic: Conformational Analysis 62. Consider the graph below, which is a plot of the relative energies of the various conformations of hexane, viewed through the C2-C3 bond. The conformations corresponding to the 60o and 300o are:
Relative energy

64. Which conformation of trans-1-isopropyl-3-methylcyclohexane would be present in greatest amount at equilibrium? A) The conformation with the methyl group equatorial and the isopropyl group axial B) The conformation with the methyl group axial and the isopropyl group equatorial C) The conformation with both groups axial D) The conformation with both groups equatorial E) The twist boat conformation. 65. Which conformation represents the most stable conformation of trans-1-bromo-4methylcyclohexane?
CH3 Br Br Br H3C CH3 Br

0o

60o 120o 180o 240o 300o 360o

Angle of rotation

A) B) C) D) E)

Eclipsed Staggered, and gauche Staggered and anti More stable than the conformation at 180o None of the above

Br

II

CH3

CH3

III

IV

63. Consider the graph below, which is a plot of the relative energies of the various conformations of 2,3-dimethylbutane, viewed through the C2-C3 bond. The conformations corresponding to the 120o and 240o are:
Relative energy

A) B) C) D) E)

I II III IV V

Topic: Cis-Trans Isomers 66. Which of the following can be described as cis isomers?
Br Cl Br CH3 HO CH3 CH2CH3

HO

I
0o 60o 120o 180o 240o 300o 360o

II

CH3

III

IV

A) B) C) D) E)

Angle of rotation Eclipsed, more stable than the conformation at 0o Eclipsed, more stable than the conformation at 180o Staggered, more stable than the conformation at 0o Staggered, less stable than the conformation at 180o Two of the above are true

A) B) C) D) E)

I II, V III, IV I, III and IV None of the above are cis isomers.

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67. Which of the following can be described as trans isomers?

Br Cl Br CH3 HO CH3 CH2CH3

Topic: Conformational Analysis 71. A) B) C) D) E) The twist boat conformation is the preferred conformation for this compound. cis-1,4-Di-tert-butylcyclohexane trans-1,4-Di-tert-butylcyclohexane cis-1,3-Di-tert-butylcyclohexane trans-1,2-Di-tert-butylcyclohexane None of these

HO

II

CH3

III

IV

A) B) C) D) E)

I II, V III, IV I, III and IV None of the above are trans isomers.

Topic: Ring Strain 72. Which of these C10H18 isomers is predicted to be the most stable?
H

Topic: Conformational Analysis 68. Which of the following will have the same energy after undergoing ring flip?
OH Cl Br CH3 HO CH2CH3 CH2CH3

II

III

IV

HO

II

CH3

III

IV

A) B) C) D) E)

I II III IV V Ans: E

A) B) C) D) E) 69. A) B) C) D) E)

I II III IV V. The least stable conformation of cyclohexane is the: boat. twist boat. chair. half-chair. twist chair.
CH3 H3C CH3 H3C

Topic: General 75. A) B) C) D) E) How many constitutional isomers are possible for the formula C6H14? 2 3 4 5 6

70. Express, quantitatively, the difference in stability of the two structures shown below.

76. How many compounds with the formula C7H16 (heptanes) contain a single 3 carbon atom? A) 2 B) 3 C) 4 D) 5 E) 6

II

A) B) C) D) E)

I is more stable than II by 7.5 kJ mol-1. I is more stable than II by 15 kJ mol-1. II is more stable than I by 7.5 kJ mol-1. II is more stable than I by 15 kJ mol-1. The two are equal in stability.

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Topic: Alkane Synthesis, Nomenclature 77. Catalytic hydrogenation of which of the following will yield 2-methylpentane? A) 2-methyl-1-pentene B) 2-methyl-2-pentene C) 4-methyl-2-pentene D) 4-methyl-1-pentene E) All of the above
2

SHORT ANSWER QUESTIONS Topic: Nomenclature 92. Give the IUPAC name corresponding to the following structure.
Br

Topic: Alkane Synthesis, Nomenclature 78. The synthesis of an alkyne precursor to 2,2-dimethylheptane is accomplished most effectively by the reaction between these two reagents: A) CH3CH2CH2C!CNa and (CH3)3CBr B) CH3CH2C!CNa and (CH3)3CCH2Br C) (CH3)3CC!CNa and CH3CH2CH2Br D) (CH3)3CCH2CH2C!CH and CH3CH2I E) HC!CNa and (CH3)3CCH2CH2Br 79. The reaction of the Na salt of 3-methyl-1-pentyne with 1-bromo-3-methylbutane produces which of these? A) 3,8-dimethyl-4-nonyne B) 2,7-dimethyl-4-nonyne C) 3,8-dimethyl-5-nonyne D) 3,7-dimethyl-4-nonyne E) 3,7-dimethyl-5-nonyne Topic: General 80. What is the simplest alkane, i.e., the one with the smallest molecular weight, which possesses primary, secondary and tertiary carbon atoms? A) 2-Methylpropane B) 2-Methylbutane C) 2-Methylpentane D) 3-Methylpentane E) 2,2-Dimethylbutane 81. A) B) C) D) E) How many alkanes of formula C7H16 possess a quaternary carbon atom? 1 2 3 4 5

OH

93. Give the IUPAC name corresponding to the following structure:

Br HO

94.

Give the IUPAC name corresponding to the following structure:

Br F

95. Give the IUPAC name corresponding to the following structure:

HO

96. Draw the bond-line structural formula corresponding to the most stable conformation of the following substance: trans-1-bromo-3-(1-methylpropyl)cyclohexane 97. Draw the bond-line structural formula corresponding to the name: 2,5,9-trimethyl-2decen-7-yne Topic: Alkane Conformations 98. Draw the Newman projection formula for the gauche conformation of the C2-C3 bond in pentane. 99. Draw the Newman projection formula for the most stable conformation of the C2-C3 bond in 3-methylpentane.

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Svar Test banken Solomons Chapt. 4

Frga 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 Svar C D E D E C D D A A D A C A D E A D A A D C C C B E C D E B E E C D C B E A E B Rtt/Fel Frga 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 Svar D B A D A A A C C C A E D D B D B A C D E B A B A B C E D A A E A A D C E C A B C Rtt/Fel

92. 93. 94. 95. 96: 97:

5-bromo-6-cyclopentyl-2-hexanol 3-(2-bromobutyl)cyclopentanol trans-1-bromo-2-fluorocyclohexane 3-ethyl-6,7-dimethyl-2-octanol

Br

98:

CH3 H H

CH2CH3 H

99:

H CH3

H H

CH3 H

CH2CH3

107

108