Chapter Four

MULTIPLE CHOICE QUESTIONS Topic: Nomenclature Section: 4.2 Difficulty Level: Easy 1. 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 Ans: E

Topic: General Section: 4.2 Difficulty Level: Easy 2. A) B) C) D) E) How many constitutional isomers are possible for the formula C6H14? 2 3 4 5 6 Ans: D

Topic: General Section: 4.2 and 4.3 Difficulty Level: Easy 3. 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 Ans: B

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Topic: General Section: 4.2 and 4.3 Difficulty Level: Medium 4. A) B) C) D) E) How many alkanes of formula C7H16 possess a quaternary carbon atom? 1 2 3 4 5 Ans: C

Topic: Nomenclature Section: 4.3B Difficulty Level: Easy 5.

A) B) C) D) E)

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 Ans: C

is:

Topic: Nomenclature Section: 4.3B Difficulty Level: Medium 6.

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 Ans: D

is:

174

Topic: Nomenclature Section: 4.3B Difficulty Level: Medium 7. A correct IUPAC name for the following compound is:

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 Ans: E

Topic: Nomenclature Section: 4.3C Difficulty Level: Easy 8. A) B) C) D) E) Which of these is the common name for the 1,1-dimethylpropyl group? tert-Butyl tert-Pentyl Isopentyl Neopentyl sec-Pentyl Ans: B

Topic: Nomenclature Section: 4.3C Difficulty Level: Medium 9. A) B) C) D) E) CH3CHCH2 CH2CH3 is: An IUPAC name for the group Isopentyl Isoamyl sec-Butylmethyl 2-Methylbutyl 2-Ethylpropyl Ans: D

175

Topic: Nomenclature Section: 4.3C Difficulty Level: Medium 10. A) B) C) D) E) The neopentyl group has the alternative name: 1,1-Dimethylpropyl 1,2-Dimethylpropyl 2,2-Dimethylpropyl 1-Methylbutyl 2-Methylbutyl Ans: C

Topic: Nomenclature Section: 4.3C Difficulty Level: Medium 11. Isopentyl is the common name for which alkyl group? A) CH3CH2CH2CH CH3 B) CH3CH2CHCH2 CH3 C) CH3CHCH2CH2 CH3 CH3CH2CH D) E) CH3 CH3 Ans: C CH2CH3

CH3CCH2

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Topic: Nomenclature Section: 4.3C Difficulty Level: Hard 12. 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 Ans: E Topic: Nomenclature Section: 4.3B/C Difficulty Level: Easy 13. What is a correct name for the following compound?

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 Ans: E

Topic: Nomenclature Section: 4.3B/C Difficulty Level: Medium 14.

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 Ans: D

is:

177

Topic: Nomenclature Section: 4.3B/C Difficulty Level: Medium 15. An IUPAC name for the following compound is:

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 Ans: C

Topic: General Section: 4.2, 4.3D Difficulty Level: Medium 16. How many compounds with the formula C7H16 (heptanes) contain a single 3 carbon atom? A) 2 B) 3 C) 4 D) 5 E) 6 Ans: C Topic: Nomenclature Section: 4.3E Difficulty Level: Easy 17. What is the common name for this compound?
Br

A) B) C) D) E)

Isobutyl bromide tert-Butyl bromide Butyl bromide sec-Butyl bromide Bromo-sec-butane Ans: A

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Topic: Nomenclature Section: 4.3E Difficulty Level: Medium 18.

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 Ans: C

A) B) C) D) E)

Topic: Nomenclature Section: 4.3F Difficulty Level: Easy 19. What is the correct IUPAC name for the following compound?
HO

A) B) C) D) E)

3-Hydroxymethylheptane 3-Hydroxymethylhexane 3-Methyloxyheptane 2-Ethyl-1-hexanol 2-Ethyl-1-heptanol Ans: D

Topic: Nomenclature Section: 4.3F Difficulty Level: Easy 20. What is the correct IUPAC name for the following compound?
OH

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 Ans: E

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Topic: Nomenclature Section: 4.3F Difficulty Level: Easy 21. What is the correct IUPAC name for the following compound?
OH F

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 Ans: E

Topic: Nomenclature Section: 4.3F Difficulty Level: Medium 22. 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 Ans: C Topic: Nomenclature Section: 4.3B/E/F Difficulty Level: Medium 23. A correct IUPAC name for the following compound is:

OH

Cl

A) B) C) D) E) Ans:

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 D

180

Topic: Nomenclature Section: 4.3F and 4.4 Difficulty Level: Hard 24. The correct IUPAC name for the following compound is:
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 Ans: B

181

Topic: Conformational Analysis Section: 4.4A Difficulty Level: Medium 25. 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 Br CH3 CH3 CH3 H H3C Br H CH3 CH2CH3 H H H Br CH3 CH(CH3)2

I
CH3 Br H H CH2CH3 CH3

II
CH3 Br H H

III

CH3 CH2CH3

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

182

Topic: Conformational Analysis Section: 4.4A Difficulty Level: Medium 26. The least 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):
CH3 Br H H H CH(CH3)2 Br H CH3 H CH3 CH2CH3 H H CH3 Br CH2CH3 CH3

I
H Br H H

II
CH(CH3)2 CH3 H H Br H

III

CH3 CH(CH3)2

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

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Topic: Conformational Analysis Section: 4.4A Difficulty Level: Medium 27. 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
CH3 H H3CH2C CH3 H CH3

II
H3C H CH3 H

III

CH3 CH(CH3)2

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

184

Topic: Conformational Analysis Section: 4.4A Difficulty Level: Medium 28. The least 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 H H3C CH3 H CH2CH3 CH3

I
H H H3C H3C CH2CH3 CH3

II
CH3 H3C H H

III

CH3 CH(CH3)2

IV

A) B) C) D) E)

I II III IV V Ans: D

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Topic: Nomenclature Section: 4.4B Difficulty Level: Easy 29. Which of the following is bicyclo[3.2.2]nonane?

II

III

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

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Topic: Nomenclature Section: 4.4B Difficulty Level: Easy 30. Which compound is a bicycloheptane?

II

III

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

Topic: Nomenclature Section: 4.4B Difficulty Level: Easy 31. Which is the correct name for the compound shown below? A) B) C) D) E) Bicyclo[2.2.0]hexane Bicyclo[2.2.0]butane Bicyclo[2.2.2]hexane Bicyclo[2.2.1]hexane Disquarane Ans: A

187

Topic: Nomenclature Section: 4.4B Difficulty Level: Easy 32. What is the name of this compound?

A) B) C) D) E)

Bicyclo[2.2.2]octane Bicyclo[3.2.1]octane Bicyclo[4.1.1]octane Bicyclo[4.2.0]octane Bicyclo[3.3.0]octane Ans: D

Topic: Nomenclature Section: 4.4B Difficulty Level: Easy

II

III

IV 33. A) B) C) D) E)

Which of the above is bicyclo[3.3.1]nonane? I II III IV V Ans: D

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Topic: Nomenclature Section: 4.4B Difficulty Level: Easy

II

III

IV 34. A) B) C) D) E)

Which of the above is bicyclo[5.2.0]nonane? I II III IV V Ans: E

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Topic: Nomenclature Section: 4.4B Difficulty Level: Easy

II

III

35. A) B) C) D) E)

IV V Which of the above is bicyclo[4.3.0]nonane? I II III IV V Ans: A

Topic: Nomenclature Section: 4.4B Difficulty Level: Easy 36. Which of the following structures represents bicyclo[3.2.1]octane?

II

III

A) B) C) D) E)

I II III IV V Ans: E

IV

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Topic: Nomenclature Section: 4.4B Difficulty Level: Hard 37. A correct name for the following compound is:

A) B) C) D) E)

2-Methylbicyclo[4.3.0]nonane 1-Methylbicyclo[4.3.1]nonane 7-Methylbicyclo[4.3.0]nonane 2-Methylbicyclo[4.3.1]nonane 1-Methylbicyclo[4.3.0]nonane Ans: A

Topic: Nomenclature Section: 4.4B Difficulty Level: Hard 38. What is the correct name of the following compound?
Cl

A) B) C) D) E)

1-Chlorobicyclo[4.1.1]octane 2-Chlorobicyclo[4.1.0]octane 2-Chlorobicyclo[4.1.1]octane 2-Chlorobicyclo[4.1.1]heptane 5-Chlorobicyclo[4.1.1]octane Ans: C

Topic: Nomenclature Section: 4.4B Difficulty Level: Hard 39. A correct name for the following compound is:
Cl

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 Ans: A

191

Topic: Nomenclature Section: 4.4B Difficulty Level: Hard 40. A correct name for the following compound is:
Br

A) B) C) D) E)

4-bromo-3,8-dimethylbicyclo[5.2.2]nonane 3,8-dimethyl-4-bromo-bicyclo[5.2.0]nonane 4-bromo-3,8-dimethylbicyclo[5.2.1]decane 7-bromo-2,6-dimethylbicyclo[5.2.0]nonane 4-bromo-3,8-dimethylbicyclo[5.2.0]nonane Ans: E

Topic: Nomenclature Section: 4.5 Difficulty Level: Medium 41. A correct IUPAC name for the following compound is:
Br

A) B) C) D) E) Ans:

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 4-bromo-6-isopropyl-3,6-dimethyl-1-hexene C

192

Topic: Nomenclature Section: 4.5 Difficulty Level: Hard 42. What is the correct IUPAC name for the following compound?

HO

A) B) C) D) E)

trans-3-Hydroxymethyl-2-heptene trans-2-(1-methylethyl)-4-hexen-1-ol trans-5-(1-methylethyl)-2-hexen-6-ol cis-5-isopropyl-2,6-hexenol cis-2-(1-methylethyl)-4-hepten-1-ol Ans: B

Topic: Nomenclature Section: 4.6 Difficulty Level: Easy 43. Give the IUPAC name for

A) B) C) D) E)

3-Methyl-4-hexyne 4-Methyl-2-hexyne 2-Ethyl-3-pentyne 4-Ethyl-2-pentyne 3-Methyl-2-hexyne Ans: B

Topic: Nomenclature Section: 4.6 Difficulty Level: Easy 44. A) B) C) D) E) The IUPAC name for diisobutylacetylene is 2,7-Dimethyl-4-octene 2,7-Dimethyl-4-octyne 3,6-Dimethyl-4-octyne 2,5-Diethyl-3-hexyne 2,2,5,5-Tetramethyl-3-hexyne Ans: B

193

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Easy 45. The least stable conformation of butane is:
H H3C H3C H H H H H H H CH3 CH3 H H3C H H CH3 H

I
H H H H CH3 CH3

II
CH3 H H H CH3 H

III

A) B) C) D) E)

I II III IV V Ans: B

IV

194

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Easy 46. The most stable conformation of butane is:
H H3C H3C H H H H H H H CH3 CH3 H H3C H H CH3 H

I
H H H H CH3 CH3

II
CH3 H H H CH3 H

III

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

195

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Easy 47. The least stable conformation of butane is:
H H3C H3C H H H H H H H CH3 CH3 H H3C H H CH3 H

I
H H H H CH3 CH3

II
CH3 H H H CH3 H

III

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

196

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Easy 48. 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

I
H H H H Br Br

II
Br H H H Br H

III

A) B) C) D) E)

I II III IV V Ans: C

IV

197

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Medium 49. Which conformation(s) of 1,2-dibromoethane does not illustrate one or more gauche interactions?
H Br Br H H H H H H H Br Br H H Br H Br H

I
H H H H Br Br

II
Br H H H Br H

III

A) B) C) D) E)

I and II only II, III, and V only I, III, and IV only All but one above All the above Ans: D

IV

198

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Medium 50. 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

I
H Br H H

II
CH3 CH(CH3)2 CH3 Br H H

III

CH3 CH2CH3

A) B) C) D) E)

I II III IV V Ans: A

IV

199

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Medium 51. 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 CH3

I
Br H3C H3C Br H H

II
Br H H3C CH3 Br H

III

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

200

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Medium 52. Which conformation(s) show(s) the bromines in a gauche orientation for 2,3dibromobutane, viewed through the C-2C-3 bond?
CH3 Br Br CH3 H H H3C H3C H H Br Br H H3C Br H Br CH3

I
Br H3C H3C Br H H

II
Br H H3C CH3 Br H

III

IV A) B) C) D) E) I and II only III and IV only I and V only II only None of the above Ans: C

201

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Medium 53. The least 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 Br H CH3 H CH3 CH2CH3 H H CH3 Br CH2CH3 CH3

I
H Br H H

II
CH(CH3)2 CH3 H H Br H

III

CH3 CH(CH3)2

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

202

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Medium 54. Consider the graph below, which is a plot of the relative energies of the various conformations of hexane, viewed through the C-2C-3 bond. The conformations corresponding to the 60o and 300o are:
Relative energy
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 Ans: B

203

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Medium 55. Consider the graph below, which is a plot of the relative energies of the various conformations of 2,3-dimethylbutane, viewed through the C-2C-3 bond. The conformations corresponding to the 120o and 240o are:
Relative energy
0o 60o 120o 180o 240o 300o 360o

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 Ans: A

204

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Hard 56. Which staggered Newman projection(s), looking down the C-2C-3 bond (C-2 in front and C-3 in back), illustrates the following boxed compound?

OH H3C HO CH3 H HO H3C CH=CH2 H H H3C H CH3 H

H CH=CH2

I
CH3 H HO CH3 H CH=CH2

II

CH3 CH3 H H

OH CH=CH2

III
CH3 OH CH=CH2

IV A) B) C) D) E) I, II and V II and V III and IV V only None of the above Ans: B

205

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Hard 57. Which staggered Newman projection(s), looking down the C-2C-3 bond (C-2 in front and C-3 in back), illustrates the following boxed compound?
Cl

H H3C

CH2CH3 Cl H CH3

Cl H3C

CH2CH3 H H

CH3 H Cl

CH3

I
H3C H CH2CH3 Cl H

II

CH3 H H H H H

H CH2CH3

III

IV A) B) C) D) E) I, II and III II and V I and II V only None of the above Ans: E

CH3

CH(CH3)CHClCH3

206

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Hard 58. Which staggered Newman projection(s), looking down the C-3C-4 bond (C-3 in front and C-4 in back), illustrate(s) the following boxed compound?

OH

HO H

CH2CH(CH3)2 H CH3 CH2CH3

HO H3C

CH2CH(CH3)2 H H CH2CH3

H HO

CH2CH3 CH3 H CH2CH(CH3)2

I
H3CH2C H CH2CH(CH3)2 OH CH3

II

III
H HO H3C H CH2CH(CH3)2 CH2CH3

IV A) B) C) D) E) I, II and III II and V I and II III only None of the above Ans: D

207

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Hard 59. Which staggered Newman projection(s), looking down the C-2C-3 bond (C-2 in front and C-3 in back), illustrate(s) the following boxed compound?
Cl Br

H Cl

CH2CH2CH3 Br H CH3

H H

CH2CH2CH3 Br Cl

CH3 Cl Br

H H

I
H H Cl Br

II

CH3 H Cl H3C H

CH2CH2CH3

III
CH2CH2CH3 Br

CH2CH2CH3

IV A) B) C) D) E)

CH3

I only II and V I and II III only None of the above Ans: A

208

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Hard 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) Ans: D

209

Topic: Conformational Analysis Section: 4.8A Difficulty Level: Hard 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

A) B) C) D) E)

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

Topic: Conformational Analysis Section: 2.13 and 4.8A Difficulty Level: Medium 62. 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

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. Ans: C

210

Topic: Ring Strain Section: 4.10 Difficulty Level: Easy 63. A) B) C) D) E) Which cycloalkane has the greatest ring strain? Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane Ans: A

Topic: Ring Strain Section: 4.10 Difficulty Level: Easy 64 Which cycloalkane has the least ring strain? . A) B) C) D) E) Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane Ans: D

Topic: Ring Strain Section: 4.11 Difficulty Level: Easy 65. A) B) C) D) E) Which is the most stable conformation of cyclohexane? Chair Twist Boat One-half chair Staggered Ans: A

211

Topic: Conformational Analysis Section: 4.11 Difficulty Level: Easy 66. A) B) C) D) E) The least stable conformation of cyclohexane is the: boat. twist boat. chair. half-chair. twist chair. Ans: D

Topic: Conformational Analysis Section: 4.12 Difficulty Level: Medium 67 The preferred conformation of cis-3-tert-butyl-1-methylcyclohexane is the one in which: . A) B) C) D) E) 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. Ans: D

Topic: Nomenclature Section: 4.13 Difficulty Level: Easy 68. Select the systematic name for
Cl H H Cl

A) B) C) D) E)

cis-1,3-Dichlorocyclopentane trans-1,4-Dichlorocyclopentane cis-1,2-Dichlorocyclopentane trans-1,3-Dichlorocyclopentane 1,1-Dichlorocyclopentane Ans: D

212

Topic: Nomenclature Section: 4.13 Difficulty Level: Medium

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

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

II

III

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

Topic: Nomenclature Section: 4.13 Difficulty Level: Medium

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

I 70. A) B) C) D) E)

II

III

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

213

Topic: Nomenclature Section: 4.13 Difficulty Level: Medium 71. 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)

I II III II and III I and II Ans: A

II

III

Topic: Conformational Analysis Section: 4.13 Difficulty Level: Medium 72. What structure represents the most stable conformation of cis-1,3-dimethylcyclohexane?
CH3 H3C H H H3C H H CH3 H CH3 CH3 H

I
H CH3 H

II
H H3C H

III
CH3

H3C

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

214

Topic: Conformational Analysis Section: 4.13 Difficulty Level: Medium 73. 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 Ans: A

Topic: Nomenclature Section: 4.5, 4.13 Difficulty Level: Easy 74. Select the structure for cis-3-methyl-6-vinylcyclohexene.

II

III

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

215

Topic: Conformational Analysis Section: 4.11, 4.12, and 4.13 Difficulty Level: Medium 75. 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. Ans: B Topic: Conformational Analysis Section: 4.11, 4.12, and 4.13 Difficulty Level: Medium 76. 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. Ans: D Topic: Conformational Analysis Section: 4.11, 4.12, and 4.13 Difficulty Level: Medium 77. 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. Ans: B

216

Topic: Conformational Analysis Section: 4.11, 4.12, and 4.13 Difficulty Level: Medium 78. 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 Ans: A

Topic: Conformational Analysis Section: 4.11, 4.12, and 4.13 Difficulty Level: Medium . 79 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. Ans: B

217

Topic: Conformational Analysis Section: 4.11, 4.12, and 4.13 Difficulty Level: Medium 80. Which conformation represents the most stable conformation of trans-1-bromo-4methylcyclohexane?
Br CH3 Br Br

I
Br H3C

II

CH3 CH3

CH3

III
Br

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

Topic: Conformational Analysis Section: 4.11, 4.12, and 4.13 Difficulty Level: Medium

218

81. Which of the following will have the same energy after undergoing ring flip?
HO OH Cl Br

I
CH3 HO

II

CH3 CH2CH3

III
CH2CH3

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

Topic: Cis-Trans Isomers Section: 4.12 and 4.13 Difficulty Level: Easy 82. Which of the following can be described as cis isomers?
HO Br Cl Br

I
CH3 HO

II

CH3 CH3

III
CH2CH3

IV A) B) C) D) E)

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

Topic: Cis-Trans Isomers Section: 4.12 and 4.13 Difficulty Level: Easy

219

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

HO Br Cl Br

I
CH3 HO

II

CH3 CH3

III
CH2CH3

IV A) B) C) D) E)

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

Topic: Ring Strain Section: 4.14 Difficulty Level: Medium 84. Which of these C10H18 isomers is predicted to be the most stable?

I
H

II
H

III

A) B) C) D) E)

I II III IV V Ans: E

IV

Topic: Alkane Synthesis Section: 4.16 Difficulty Level: Easy

220

85. A) B) C) D) E)

Select the reagents necessary to convert cyclopentene into cyclopentane. H2 and Ni H2O Heat Zn, H3O+ Light Ans: A

Topic: Catalytic hydrogenation Section: 4.16 Difficulty Level: Easy 86. Which alkene would yield 3-methylpentane when subjected to catalytic hydrogenation? A) B) C) D) E) Ans: B Topic: Alkane Synthesis, Nomenclature Section: 4.16A Difficulty Level: Medium

221

87. A) B) C) D) E)

Catalytic hydrogenation of which of the following will yield 2-methylpentane? 2-methyl-1-pentene 2-methyl-2-pentene 4-methyl-2-pentene 4-methyl-1-pentene All of the above Ans: E
2

Topic: Alkane Synthesis, Nomenclature Section: 4.16A Difficulty Level: Medium 88. A) B) C) D) E) How many moles of hydrogen (H2) will react with (trans, trans)-hepta-3,5-dien-1-yne? 1 2 3 4 5 Ans: D
2

Topic: Alkane Synthesis, Nomenclature Section: 4.16A Difficulty Level: Medium 89. A) B) C) D) E) How many moles of hydrogen (H2) will react with 3-cyclobutylpropan-1-ol? 1 2 3 4 None of the above Ans: E
2

Topic: Alkane Synthesis, Nomenclature Section: 4.16A Difficulty Level: Medium

222

90. A) B) C) D) E)

How many moles of hydrogen (H2) will react with 5-chlorocyclohex-3-en-1-ol? 1 2 3 4 None of the above Ans: A
2

Topic: Alkane Synthesis, Nomenclature Section: 4.16A Difficulty Level: Medium 91. A) B) C) D) E) How many moles of hydrogen (H2) will react with cylohexa-2,5-diene-1,4-diol? 1 2 3 4 None of the above Ans: B
2

Topic: Alkane Synthesis, Nomenclature Section: 4.16A Difficulty Level: Medium 92. A) B) C) D) E) How many moles of hydrogen (H2) will react with 3-vinylcyclo-2-penten-1-ol? 0 1 2 3 4 Ans: C
2

Topic: Alkane Synthesis, Nomenclature Section: 4.16A Difficulty Level: Medium

223

93. A) B) C) D) E)

How many moles of hydrogen (H2) will react with trans-1,2-dimethylcyclohexane? 0 1 2 3 4 Ans: A
2

Topic: Alkane Synthesis, Nomenclature Section: 4.16A Difficulty Level: Medium 94. A) B) C) D) E) How many moles of hydrogen (H2) will react with cis-2,3,3-trimethylhepta-1,5-diene? 0 1 2 3 4 Ans: C
2

Topic: Alkane Synthesis, Nomenclature Section: 4.3 and 4.16A Difficulty Level: Easy 95. What product is formed when trans-1,2-dimethylcyclohexane is reacted with Pd/C and H2? A) No reaction B) cis-1,2-dimethylcyclohexane C) trans-3,4-dimethylhexane D) trans-1,2-dimethylhexane E) None of the above Ans: A
2

Topic: Alkane Synthesis, Nomenclature Section: 4.3 and 4.16A

224

Difficulty Level: Medium 96. What product is formed when cis-2,3,3-trimethylhepta-1,5-diene is reacted with Pd/C and H2? A) cis-5,5,6-trimethylhept-2-ene B) 2,3,3-trimethylhept-1-ene C) 5,5,6-trimethylheptane D) 2-isopropyl-2-methylhexane E) None of the above Ans: E
2

Topic: Alkane Synthesis, Nomenclature Section: 4.3 and 4.16A Difficulty Level: Medium 97. A) B) C) D) E) What product is formed when 3-cyclobutylpropan-1-ol is reacted with Pd/C and H2? 3-cyclobutylpropane 1-propanol No reaction hexane None of the above Ans: C
2

Topic: Alkane Synthesis, Nomenclature Section: 4.3 and 4.16A Difficulty Level: Medium 98. A) B) C) D) E) What product is formed when 5-chlorocyclohex-3-en-1-ol is reacted with Pd/C and H2? 5-chlorocyclohexanol 3-chlorocyclohexanol 5-chloro-3-hexanol 2-chloro-4-hexanol None of the above Ans: B
2

Topic: Alkane Synthesis, Nomenclature Section: 4.3 and 4.16A

225

Difficulty Level: Medium 99. A) B) C) D) E) What product is formed when 3-vinylcyclo-2-penten-1-ol is reacted with Pd/C and H2? 3-vinylcyclopentanol 3-ethylcyclo-2-penten-1-ol 4-ethylcyclopentanol 3-ethylcyclopentanol None of the above Ans: D
2

Topic: Alkane Synthesis, Nomenclature Section: 4.3 and 4.16A Difficulty Level: Medium 100. What product is formed when 2,3,3-trimethylhept-1-en-6-yne is reacted with Pd/C and H2? A) 2,3,3-trimethylheptan-6-yne B) 2,3,3-trimethylheptan-1-ene C) 5,5,6-trimethylheptan-6-yne D) 2,3,3-trimethylheptane E) None of the above Ans: D
2

Topic: Alkane Synthesis, Nomenclature Section: 4.3 and 4.16A Difficulty Level: Hard 101. A) B) C) D) E) What product is formed when cylohexa-2,5-diene-1,4-diol is reacted with Pd/C and H2? hexane-1,4-diol cyclohexa-2-ene-1,4-diol cyclohexane-1,4-diol hexane-1,4-diol None of the above Ans: C
2

Topic: Alkane Synthesis, Nomenclature Section: 4.3 and 4.16A Difficulty Level: Hard

226

102. What product is formed when (trans, trans)-hepta-3,5-dien-1-yne is reacted with Pd/C and H2? A) heptane B) 1-heptyne C) 1-ethylpentane D) trans-2-heptene E) None of the above Ans: A
2

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Easy 103. A) B) C) D) E) What is the index of hydrogen deficiency (or degree of unsaturation) of benzene (C6H6)? 2 3 4 5 6 Ans: C

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Easy 104. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) B) C) D) E)

2 3 4 5 6 Ans: E 227

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Easy 105. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) B) C) D) E)

2 3 4 5 6 Ans: A

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Easy 106. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?
CN OH

A) B) C) D) E)

2 3 4 5 6 Ans: B

Topic: Index of Hydrogen of Deficiency

228

Section: 4.17 Difficulty Level: Easy 107. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) B) C) D) E)

2 3 4 5 6 Ans: C

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Easy 108. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?

A) B) C) D) E)

2 3 4 5 6 Ans: E

Topic: Index of Hydrogen of Deficiency 229

Section: 4.17 Difficulty Level: Easy 109. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?
O N O

A) B) C) D) E)

2 3 4 5 6 Ans: A

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Easy 110. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?
Cl O O O

A) B) C) D) E)

2 3 4 5 6 Ans: A

230

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Easy 111. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C6H2O2? A) 3 B) 4 C) 5 D) 6 E) 7 Ans: D

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Easy 112. What is the index of hydrogen deficiency (or degree of unsaturation) for retinol?
OH

A) B) C) D) E)

3 4 5 6 7 Ans: D

Topic: Index of Hydrogen of Deficiency

231

Section: 4.17 Difficulty Level: Easy 113. What is the index of hydrogen deficiency (or degree of unsaturation) for the drug lidocain?
H N O N

A) B) C) D) E)

3 4 5 6 7 Ans: C

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Easy 114. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C8H3Br5O2? A) 2 B) 3 C) 4 D) 5 E) 6 Ans: D

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Medium

232

115. What is the index of hydrogen deficiency (or degree of unsaturation) for the drug Cetilistat?
N O O O

A) B) C) D) E)

3 4 5 6 7 Ans: E

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Medium 116. What is the index of hydrogen deficiency (or degree of unsaturation) for the drug THC?
OH

A) B) C) D) E)

3 4 5 6 7 Ans: D

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Medium 233

117. What is the index of hydrogen deficiency (or degree of unsaturation) of the following molecule?
CO2CH3

A) B) C) D) E)

2 3 4 5 6 Ans: B

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Medium 118. What is the index of hydrogen deficiency (or degree of unsaturation) of the following compound?

A) B) C) D) E)

3 4 5 6 7 Ans: D

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Medium

234

119. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C21H30O5? A) 3 B) 4 C) 5 D) 6 E) 7 Ans: E Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Medium 120. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C14H14Cl4? A) 3 B) 4 C) 5 D) 6 E) 7 Ans: D Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Medium 121. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C9H18N2? A) 2 B) 3 C) 4 D) 5 E) 6 Ans: A

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Medium

235

122. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C7H7NOS? A) 2 B) 3 C) 4 D) 5 E) 6 Ans: D Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Medium 123. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C6H5BrClN? A) 0 B) 1 C) 2 D) 3 E) 4 Ans: E Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Hard 124. What is the index of hydrogen deficiency (or degree of unsaturation) of the hormone cortisol?
O HO H H O H OH OH

A) B) C) D) E)

3 4 5 6 7 Ans: E

Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Hard

236

125. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of C11H20Br3F4N3O3? A) 0 B) 1 C) 2 D) 3 E) 4 Ans: A Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Hard 126. What is the index of hydrogen deficiency (or degree of unsaturation) of a compound with the molecular formula of H6N4O3? A) 0 B) 1 C) 2 D) 3 E) 4 Ans: A Topic: Index of Hydrogen of Deficiency Section: 4.17 Difficulty Level: Hard 127. What is the index of hydrogen deficiency (or degree of unsaturation) for the drug morphine?
HO

O H HO

A) B) C) D) E)

6 7 8 9 10 Ans: D

Topic: Alkane Synthesis, Nomenclature Section: 4.16A and 4.17 Difficulty Level: Medium

237

128. Which statement(s) is/are true about a molecule with the molecular formula C10H20, that when subjected to catalytic hydrogenation there is no consumption of hydrogen? A) The molecule has no degrees of unstaturation. B) There is one degree of unsaturation, which happens to be a pi-bond. C) There are two degrees of unsaturation where one is a ring and the other is a pi-bond. D) There is one degree of unsaturation, which happens to be a ring. E) None of the above. Ans: D
2

Topic: Alkane Synthesis, Nomenclature Section: 4.16A and 4.17 Difficulty Level: Medium 129. Which statement(s) is/are true about a molecule with the molecular formula C10H14O, that when subjected to Pd/C and H2 in ethyl acetate, there is a consumption of 2 moles of hydrogen? A) The molecule has no degrees of unsaturation. B) There are four degrees of unsaturation, where two come from either two alkenes or one alkyne and the other two are either two rings or one ring and a carbonyl. C) There are two degrees of unsaturation where they were either two alkenes or one alkyne. D) There are four degrees of unsaturation, which come from a mixture of alkenes and alkynes, that is why four hydrogens are added. E) None of the above. Ans: B
2

SHORT ANSWER QUESTIONS

238

Topic: Nomenclature Section: 4.1 Difficulty Level: Easy 130 Alkanes in which some or all of the carbon atoms are arranged in a ring are called . ___________________________. Ans: cycloalkanes Topic: Nomenclature Section: 4.3 Difficulty Level: Easy 131 What is the fundamental principle of the IUPAC system of nomenclature for organic . compounds? Ans: Each different compound should have an unambiguous name. Topic: Nomenclature Section: 4.3 Difficulty Level: Easy 132 Give the IUPAC name corresponding to the following structure: .
HO

Ans: 3-ethyl-6,7-dimethyl-2-octanol Topic: Nomenclature Section: 4.3 Difficulty Level: Medium 133 Give the IUPAC name corresponding to the following structure: .
Br

Ans: 5-bromo-6-cyclopentyl-2-hexanol

OH

Topic: General Section: 4.3B Difficulty Level: Easy 239

134 To determine the parent name for an alkane, we begin by finding the . ___________________________. Ans: longest continuous chain of carbons Topic: Nomenclature Section: 4.3B Difficulty Level: Easy 135. When more than one substituent is present on the parent chain, how do we organize the names of the substituents in the name of the compound? ___________________________. Ans: alphabetical order Topic: Nomenclature Section: 4.3B Difficulty Level: Medium 136. What are the four possible parts of an IUPAC name? Ans: locant, prefix, parent name, suffix Topic: Nomenclature Section: 4.3 and 4.4A Difficulty Level: Hard 137 Give the IUPAC name corresponding to the following structure: .
Br HO

Ans: 3-(2-bromobutyl)cyclopentanol Topic: General Section: 4.4B Difficulty Level: Easy 138. A compound containing two fused or bridged rings is referred to as a ___________________________. Ans: bicycloalkane

Topic: General Section: 4.4B Difficulty Level: Easy 240

139 In a bicyclic compound, the carbon atoms common to both rings are called . ___________________________. Ans: bridgeheads Topic: General Section: 4.6 Difficulty Level: Easy 140. A compound containing a triple bond between the first two carbons in the chain is called a ___________________________. Ans: terminal alkyne Topic: Nomenclature Section: 4.6 Difficulty Level: Medium . 141 Draw the bond-line structural formula corresponding to the name: 2,5,9-trimethyl-2decen-7-yne Ans:

Topic: General Section: 4.8A Difficulty Level: Easy 142. When non-bonded atoms/groups are closely positioned, the repulsive interactions between their electron clouds are referred to as ___________________________. Ans: steric hindrance

Topic: Alkane Conformations Section: 4.8A Difficulty Level: Easy

241

143 Draw the Newman projection formula for the gauche conformation of the C-2C-3 . bond in pentane. CH3 Ans:
H CH2CH3 H H H

Topic: Alkane Conformations Section: 4.8A Difficulty Level: Easy 144 Draw the Newman projection formula for the most stable conformation of the C2-C3 . bond in 3-methylpentane. CH3 Ans:
H CH3 H CH2CH3 H

Topic: General Section: 4.9A Difficulty Level: Easy 145. _____________________ have the same molecular formula and connectivity but different arrangements of atoms in three-dimensional space. Ans: Stereoisomers Topic: Nomenclature Section: 4.11 and 4.13 Difficulty Level: Easy 146 Give the IUPAC name corresponding to the following structure: .
Br F

Ans: trans-1-bromo-2-fluorocyclohexane

Topic: Nomenclature, Conformations Section: 4.11, 4.12, and 4.13 Difficulty Level: Hard

242

147 Draw the bond-line structural formula corresponding to the most stable conformation of . the following substance: trans-1-bromo-3-(1-methylpropyl)cyclohexane Br Ans:

243