4th Edition Test Bank Answers Ch.9 Alkynes

Organic Chemistry, 4e (Klein)

Chapter 9 Alkynes

1) Which of the following describes the orbital overlap of the C2–C3 sigma bond in the molecule shown?

CH3–C≡C–CH2CH3

A) sp—sp

B) sp2—sp2

C) sp3—sp3

D) p—p

E) sp3—sp

Diff: 1

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

2) Which of the following describes the orbital overlap of the C3–C4 sigma bond in the molecule shown?

H3C–C≡C–C≡C–CH3

A) sp—sp

B) sp2—sp2

C) sp3—sp3

D) p—p

E) sp3—sp

Diff: 1

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

3) Which two orbitals overlap to form the sigma bond between the carbon atoms shown?

A) sp3—sp3

B) p—p

C) sp2—sp2

D) s—s

E) sp—sp

Diff: 1

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

4) What is the hybridization of the carbon atoms numbered 1 and 2, respectively, in this structure?

A) sp3, sp2

B) sp2, sp2

C) sp, sp

D) sp2, sp

E) sp, sp2

Diff: 1

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

5) Which bond types are involved in forming the bond between these two carbon atoms?

A) three anti-bonds

B) three σ bonds

C) two σ bonds and one π bond

D) one σ bond and two π bonds

E) three π bonds

Diff: 1

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

6) Which of the following statements best describes how alkynes react?

A) The triple bond of an alkyne is electron-rich and therefore reacts as a nucleophile.

B) The triple bond of an alkyne is electron-poor and therefore alkynes react as a nucleophile.

C) Alkynes have low general reactivity and therefore do not easily act as nucleophiles or as electrophiles.

D) The triple bond of an alkyne is electron-rich and therefore reacts as an electrophile.

E) The triple bond of an alkyne is electron-poor and therefore reacts as an electrophile.

Diff: 1

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

7) Which of the following statements is true about the molecule shown?

H—C≡C—CH3

A) It contains a total of three sigma bonds.

B) It contains a total of three pi bonds.

C) The H—C≡C bond angle is about 109.5°.

D) The C≡C—C bond angle is 180°.

E) All carbon-carbon bonds are of equal length.

Diff: 1

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

8) What is the shape of the molecule shown?

H—C≡C—H

A) tetrahedral

B) linear

C) trigonal pyramidal

D) bent

E) trigonal bipyramidal

Diff: 1

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

9) What is the IUPAC name for the molecule shown?

A) 6-bromo-3-octyne

B) 6-bromo-6-methyl-3-heptyne

C) 2-bromo-2-methyl-4-heptyne

D) 6-bromo-6,6-dimethyl-3-hexyne

E) 2-bromo-4-octyne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

10) What is the IUPAC name for the molecule shown?

A) 1,1-diethyl-2-pentyne

B) 3-(1-butynyl)pentane

C) 5-ethyl-3-octyne

D) 3-ethyl-4-heptyne

E) 5-ethyl-3-heptyne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

11) What is the IUPAC name for the molecule shown?

A) 2-methyl-5-propyl-3-heptyne

B) 5-ethyl-2-methyl-3-octyne

C) 1-isopropyl-3-ethyl-1-hexyne

D) 6-methyl-3-propyl-4-heptyne

E) 4-ethyl-7-methyl-5-octyne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

12) What is the IUPAC name for the molecule shown?

A) 2,2,3-trimethyl-4-hexyne

B) 4-tert-butyl-2-pentyne

C) 4,5,5-trimethyl-2-hexyne

D) 4,5,5,5-tetramethyl-2-pentyne

E) 2,2-dimethyl-3-(1-propynyl)butane

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

13) What is the IUPAC name for the molecule shown?

A) 5,6,6-trimethyl-1-heptyne

B) 5-tert-butyl-1-hexyne

C) 2,2,3-trimethyl-6-heptyne

D) 2,2,3-(3-butynyl)butane

E) sec-butyl-tert-butylacetylene

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

14) What is the IUPAC name for the molecule shown?

A) 1,1,1-trichloro-4-hexyne

B) 4,4,4-trichloro-1-butyne

C) 1,1,1-trichloro-2-butyne

D) 5,5,5-trichloro-2-pentyne

E) 6,6,6-trichloro-2-hexyne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

15) What is the IUPAC name for the molecule shown?

A) 4,4-dimethyl-2-pentyne

B) 2,2-dimethyl-4-heptyne

C) 1-tert-butyl-3-heptyne

D) 6,6-dimethyl-3-heptyne

E) 6,6,6-trimethyl-3-hexyne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

16) What is the IUPAC name for the molecule shown?

A) 4-ethyl-2-pentyne

B) 2-ethyl-3-pentyne

C) 3-methyl-4-hexyne

D) 4-methyl-2-hexyne

E) sec-Butylpropyne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

17) Which of the following is a structure for hepta-3,6-dien-1-yne?

A) I

B) II

C) III

D) Iv

E) V

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

18) Which of the following is the structure for 2-hexyne?

A) I

B) II

C) III

D) IV

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

19) Which of the following is the structure for 3-sec-butyl-1-heptyne?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

20) Provide the IUPAC name for BrCH2CH2C≡CCH2CH3.

A) 1-bromo-3-hexyne

B) 6-bromo-3-hexyne

C) 1-bromo-2-hexyne

D) 6-bromo-4-hexyne

E) 1-bromo-4-hexyne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

21) Provide the IUPAC name for HC≡CCH2CH2CH3.

A) pentyne

B) 1-pentyne

C) butyne

D) 1-butyne

E) 2-butyne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

22) Provide the IUPAC name for Cl3CCH2CH2CH2C≡CH.

A) 6,6,6-trichloro-1-hexyne

B) 1,1,1-trichloro-5-hexyne

C) 5,5,5-trichloro-1-pentyne

D) 1-heptyne

E) trichlorobutylacetylene

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

23) Provide the IUPAC name for Cl3C(CH2)4C≡CH.

A) 4,4,4-trichloro-1-butyne

B) 1,1,1-trichloro-6-heptyne

C) 1,1,1-trichloro-5-heptyne

D) 6,6,6-trichloro-1-hexyne

E) 7,7,7-trichloro-1-heptyne

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

24) Provide the IUPAC name for (CH3)2CHC≡CCH2C(CH3)3.

A) 1,1,5,5,5-pentamethyl-2-pentyne

B) 1,1,1,5,5-pentamethyl-3-pentyne

C) 2,2,6-trimethyl-4-heptyne

D) 2,6,6-trimethyl-3-heptyne

E) tert-butylisopropylacetylene

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

25) Provide the systematic IUPAC name for (CH3)3CCH2C≡CCH2CH(CH3)CH2CH3.

A) 2,7,7-trimethyl-5-nonyne

B) 2-ethyl-7,7-dimethyl-4-octyne

C) 2,2,7-trimethyl-4-nonyne

D) 7-ethyl-2,2-trimethyl-4-octyne

E) 6-undecyne

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

26) What is the IUPAC name for the molecule shown?

A) 3-bromo-4-acetylenylheptane

B) 3-(1-bromopropyl)-1-hexyne

C) 3-bromo-4-propyl-5-hexyne

D) 4-bromo-3-propyl-1-hexyne

E) 4-ethynyl-5-bromo-heptane

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

27) Which of the following is the acceptable structure for (R)-5-bromohept-2-yne?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

28) What is the IUPAC name for the molecule shown?

A) (E)-5-methyl-5-hepten-1-yne

B) (Z)-5-methyl-5-hepten-1-yne

C) (E)-3-methyl-2-hepten-6-yne

D) (Z)-3-methyl-2-hepten-6-yne

E) (E)-2-butynyl-2-butene

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

29) What is the IUPAC name for the molecule shown?

A) (E)-4-isopropyloct-3-en-5-yne

B) (Z)-4-isopropyloct-3-en-5-yne

C) (E)-5-isopropyloct-5-en-3-yne

D) (Z)-5-isopropyloct-5-en-3-yne

E) (E)-4-(2-methylethyl)oct-3-en-5-yne

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

30) Which structure shown below represents (Z)-3,5-dichloro-3-hexen-1-yne?

A) I

B) II

C) III

D) IV

E) I and II

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

31) Which of the following is a structure for octa-3,6-dien-1-yne?

A) HC≡CCH=CHCH=CHCH2CH3

B) CH3CH=CHCH2C≡CC≡CH

C) CH3CH=CHCH2CH=CHC≡CH

D) CH3C≡CCH=CHCH=CHCH3

E) H2C=CHC≡CCH2CH=CHCH3

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

32) Which of the following is the structure for 2,5,5trimethylhept3yne?

A) CH3CH2CH(CH3)C≡CCH2CH(CH3)2

B) CH3CH2C(CH3)2C≡CCH(CH3)2

C) (CH3CH2)2C(CH3)C≡CCH2CH3

D) CH3CH2C(CH3)2C≡CC(CH3)3

E) CH3CH2CH2CH(CH3)C≡CC(CH3)3

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

33) What is the IUPAC name for the molecule shown below?

A) (4R,5Z)-4-chlorohept-5-en-2-yne

B) (4S,5E)-4-chlorohept-5-en-2-yne

C) (2E,4S)-4-chlorohept-2-en-5-yne

D) (2E,4R)-4-chlorohept-2-en-5-yne

Diff: 3

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

34) What is the IUPAC name for diisobutylacetylene?

A) diisopropylbutyne

B) 2,7-dimethyl-4-octyne

C) 3,6-dimethyl-4-octyne

D) 2,5-diethyl-3-hexyne

E) sec-butylacetylene

Diff: 3

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

35) What is the IUPAC name for di-sec-butylacetylene?

A) 2-ethyl-5-methyl-3-heptyne

B) 2,7-dimethyl-4-octyne

C) 3,6-dimethyl-4-octyne

D) 2,5-diethyl-3-hexyne

E) 2,2,5,5-tetramethyl-3-hexyne

Diff: 3

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

36) Which of the following are constitutionally isomeric alkynes with the molecular formula C5H8?

A) I only

B) II only

C) I and II

D) I and III only

E) I, II, and III

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

37) What name or names are appropriate IUPAC names for CH3CH(CH3)C(CH3)2C≡CCH(CH3)2?

A) 2,5,5,6-tetramethyl-3-heptyne

B) 2,5,5,6-tetramethylhept-3-yne

C) 2,5,5,6-tetramethyl-3-heptyne or 2,5,5,6-tetramethylhept-3-yne

D) 2,3,3,7-tetramethyl-4-heptyne

E) 2,3,3,7-tetramethyl-4-heptyne or 2,3,3,7-tetramethylhept-4-yne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

38) What name is an appropriate IUPAC name for CH3C≡CC(CH3)2CH(CH2CH3)2?

A) 2-ethyl-3,3-dimethylhept-2-yne

B) 5-ethyl-4,4-methyl-2-heptyne

C) 2-ethyl-3,3-dimethyl-3-heptyne

D) 5-ethyl-4,4-dimethyl-2-heptyne

E) 5-ethyl-4,4-methylhept-2-yne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

39) What is an appropriate IUPAC name for CH3CHBrC≡C(CH2)3CH3?

A) 3-bromo-2-heptyne

B) 2-bromo-3-heptyne

C) 3-bromo-2-octyne

D) 2-bromooct-2-yne

E) 2-bromo-3-octyne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

40) Provide a name for the following compound.

A) 4-sec-butyl-2-octyne

B) 5-sec-butyl-6-(2-propyne)-octyne

C) 4-butyl-3-methyl-5-heptyne

D) 4-tert-butyl-oct-2-yne

E) 2-yne-3-(1-methylpropyl)-octane

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

41) Provide an IUPAC name for the following compound.

A) 4,4-dimethylcyclododecyne

B) 9,9-dimethylcyclodecyne

C) 9,9-methylcyclodecyne

D) 4,4-dimethylcyclodecyne

E) 4,4-methylcyclodecyne

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

42) Provide an IUPAC name for the following compound.

A) 2,3-(S)-6,6-tetramethyl-oct-4-yne

B) (S)-2,3,6,6-tetramethyloct-4-yne

C) (R,S)-2,3,6,6-tetramethyl-4-octyne

D) (S,R)-2,3,6,6-tetramethyloct-4-yne

E) (R)-2,3,6,6-tetramethyloct-4-yne

Diff: 3

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

43) Provide an IUPAC name for the following compound:

A) (3Z,5E)-5-fluoro-2-methylnon-3-en-6-yne

B) (3Z,5R)-5-fluoro-2-methyl-3-nonen-6-yne

C) (3Z,5S)-5-fluoro-2-methyl-3-nonen-6-yne

D) (3E,5R)-5-fluoro-2-methylnon-3-en-6-yne

E) (3E,5S)-5-fluoro-2-methylnon-3-en-6-yne

Diff: 3

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

44) Provide an IUPAC name for the following compound.

A) (4R,5S)-4-bromo-5-chloro-3-ethylhex-1-yne

B) (4R,5S)-5-bromo-4-chloro-3-ethyl-1-hexyne

C) (4R,5S)-3-ethyl-4-bromo-5-chloro-1-hexyne

D) (4S,5S)-4-bromo-5-chloro-3-ethylhex-1-yne

E) (4R,5R)-4-bromo-5-chloro-3-ethylhex-1-yne

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

45) Which line-bond structure represents 2,5,9-trimethyl-2-decen-7-yne?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

46) Rank the following carbanions in order of increasing base strength.

A) I < II < III

B) II < III < I

C) III < II < I

D) III < I < II

E) II < I < III

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

47) Rank the following conjugate acids in order of increasing pKa.

A) I < II < III

B) II < III < I

C) III < II < I

D) III < I < II

E) II < I < III

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

48) What is the hybridization of the anionic carbon of the ion shown below?

A) sp

B) sp2

C) sp3

D) s2p

E) s2p2

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

49) Rank the following bases in order of decreasing basicity.

A) III > I > V > II > IV

B) III > V > IV > I> II

C) V > I > III > II > IV

D) III > IV > II > V > I

E) IV > II > I > III > V

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

50) Rank the following acids in order of decreasing acidity.

A) V > I > IV > II > III

B) III > IV > II > I > V

C) V > I > III > II > IV

D) I > IV > V > II > III

E) IV > I > V > II > III

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

51) Which of the circled hydrogen atoms is the most acidic?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

52) NaNH2 reacts with terminal alkynes as a ________.

A) Brønsted acid

B) Brønsted base

C) reducing agent

D) catalyst

E) electrophile

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

53) Which of the bases below would quantitatively deprotonate a terminal alkyne?

A) BuLi

B) NH3

C) NaOH

D) NaOCH2CH3

E) t-BuOK

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

54) Which of the bases below would result in the most complete deprotonation of the alkyne, shown in the reaction below?

A) NaOCH2CH3 (sodium ethoxide)

B) t-BuONa (sodium tert-butoxide)

C) NaH (sodium hydride)

D) NaHCO3 (sodium bicarbonate)

E) NaOH (sodium hydroxide)

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

55) Which statement below best explains why the Ka of acetylene is greater than that of ethylene?

A) Acetylide anions are resonance stabilized.

B) The 4 π electrons of the acetylide anion better stabilize a negative charge.

C) sp carbons stabilize a negative charge better than sp2 carbons.

D) sp2 carbons stabilize a negative charge better than sp carbons.

E) Acetylene has only two hydrogen atoms whereas ethylene has four.

Diff: 2

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

56) Select the best explanation for why methanol, CH3OH, cannot be used as a solvent for the deprotonation of a terminal alkyne by sodium amide, NaNH2.

A) Sodium amide is not a strong enough base to deprotonate the alkyne.

B) Sodium amide in methanol reduces alkynes to alkenes.

C) Methanol is a poor solvent for dissolving alkynes.

D) Methanol is more acidic than the alkyne and will be deprotonated by NaNH2.

E) Methanol is toxic and should be avoided when possible.

Diff: 2

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

57) What are the products of the reaction shown below?

CH3OH + CH3C≡C—Na+ → ?

A) CH3C≡CCH3 + Na+OH—

B) CH3C≡CH + CH3O—Na+

C) CH3C≡COCH3 + Na+OH—

D) CH3OC≡CH + Na+CH3—

E) no reaction

Diff: 2

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

58) The major result of treating 1-butyne with 6M aqueous NaOH would be ________.

A) the production of sodium alkynide

B) the production of an alkene

C) the production of an alkane

D) the production of an enol

E) no reaction

Diff: 2

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

59) Which of the circled hydrogen atoms is the least acidic?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

60) Which of the following is less basic than acetylide?

A) BuLi

B) NaNH2

C) NaOCH3

D) A and C

E) B and C

Diff: 3

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

61) Rank the following hydrocarbons in order of decreasing acidity (from most acidic to least acidic).

A) I > II > III

B) I > III > II

C) III > II > I

D) II > I > III

E) III > I > II

Diff: 1

Learning Objective: 9.3 Discuss the reasons for the enhanced acidity of acetylene and terminal alkynes compared to other hydrocarbons

62) Identify the expected major product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides

63) Identify the expected major product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides

64) Identify the major product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides

65) Select the expected major product of the reaction sequence shown.

A) 3-methylhexyne

B) 1-bromo-3-methylhexybe

C) 2-bromo-3-methylhexyne

D) 3-methyl-1-hexyne

E) 3-methyl-2-hexyne

Diff: 2

Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides

66) The most frequent method for preparing terminal alkynes using an elimination reaction involves dissolving sodium amide (NaNH2) in liquid ammonia (NH3). Which of the following statements offers the best explanation for the above statement?

A) Sodium amide deprotonates internal alkynes, which begins the series of reactions necessary reactions to generate a terminal alkyne.

B) Sodium amide irreversibly deprotonates the terminal alkyne, driving the elimination reaction to completion.

C) Sodium amide is required because it increases the stability of the terminal alkyne, stabilizing the intermediate.

D) This provides an environment in which terminal alkynes are more stable than the internal alkynes and therefore the favored product.

E) Steric hindrance favors preparation of the less substituted terminal alkyne.

Diff: 2

Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides

67) Which of the following reaction sequences can prepare 2-hexyne from acetylene?

A) 1. NaNH2; 2. CH3CH2CH2Br; 3. NaNH2; 4. CH3Br

B) 1. NaNH2; 2. CH3Br; 3. CH3CH2CH2Br;

C) 1. NaNH2; CH3Br; 3. NaNH2; 4. CH3CH2CH2Br

D) A or B

E) A or C

Diff: 1

Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides

68) A dihalide in which the halogens are attached on adjacent carbons is called a ________ dihalide.

A) vicinal

B) geminal

C) vinylic

D) allylic

E) cis

Diff: 1

Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides

69) A dihalide in which the halogens are attached on the same carbon is called a ________ dihalide.

A) vicinal

B) geminal

C) vinylic

D) allylic

E) cis

Diff: 1

Learning Objective: 9.4 Discuss the preparation of alkynes from dihalides

70) Select the expected major organic product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

71) Select the expected major organic product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

72) Select the expected major organic product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

73) What will be produced through the reaction of an internal alkyne with sodium and ammonia?

A) a cis alkene

B) a trans alkene

C) a diene

D) an alkyne

E) an alkane

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

74) What will be produced through the reaction of an internal alkyne with hydrogen and Lindlar's catalyst?

A) a cis alkene

B) a trans alkene

C) a diene

D) an alkyne

E) an alkane

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

75) What will be produced through the reaction of an alkyne with hydrogen and a metal catalyst?

A) a cis alkene

B) a trans alkene

C) a diene

D) an alkyne

E) an alkane

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

76) Select the expected major organic product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

77) Select the expected major organic product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

78) Select the expected major organic product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

79) Select the expected major organic product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

80) Select the expected major organic product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

81) Select the expected major organic product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

82) How many moles of hydrogen are required for the complete reduction of 1 mole of (3E,5Z)-3-methylhepta-3,5-dien-1-yne?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

83) Select the reagent(s) needed to accomplish the reaction shown.

A) H2, Ni

B) H2, Ni2B

C) Na, NH3(l)

D) A or B

E) B or C

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

84) Select the best reagent(s) to convert 3-heptyne to cis-3-heptene.

A) NaNH2, NH3

B) Na, NH3

C) H2, Lindlar's catalyst

D) A and C

E) B and C

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

85) Which of the reagents shown would convert 2-pentyne to trans-2-pentene?

A) NaNH2, NH3

B) Na, NH3

C) H2, Lindlar's catalyst

D) H2, Pd/C

E) H2O, HgSO4/H2SO4

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

86) Select the best reagent(s) to convert 3-heptyne to trans-3-heptene.

A) Na/NH3

B) 1 eq. NaNH2, NH3

C) excess NaNH2, NH3

D) H2/Pt

E) H2/Lindlar's catalyst

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

87) Select the reagent(s) needed to accomplish the reaction shown.

A) H2, Pd

B) H2, Lindlar's catalyst

C) Na, NH3(l)

D) A or B

E) B or C

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

88) Which of the compounds shown will be produced by the reaction of 3,4,5-trimethyl-4-hexen-1-yne with H2 and Pd/C?

A) 2,3,4-trimethylhexane

B) 3,4,5-trimethylhexane

C) 2,3,4-trimethyl-1-hexene

D) 3,4,5-trimethyl-1-hexyne

E) 2,3,4-trimethyl-5-hexyne2

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

89) To convert 1 mole of 4-methyl-1-pentyne into 2-methylpentane, the best option would be to add ________.

A) H2, Lindlar's catalyst

B) Na, NH3(l)

C) 2 moles of HCl

D) 2 moles H2, Pt

E) 1 mole H2, Pt

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

90) Which of the reagents shown would be expected to convert 2-pentyne to (Z)-2-pentene?

A) H2, Pt

B) Na, NH3

C) H2, Lindlar's catalyst

D) excess HCl

E) HgSO4, H2O

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

91) What is the expected major product of the reaction shown?

A) 2-methylhexane

B) (Z)-2-methyl-4-hexene

C) (E)-2-methyl-4-hexene

D) (Z)-5-methyl-2-hexene

E) (E)-5-methyl-2-hexene

Diff: 2

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

92) Select the reagent(s) needed to accomplish the reaction shown below.

A) H2, Ni

B) H2, Ni2B

C) H2, Lindlar's catalyst

D) A and B

E) B and C

Diff: 2

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

93) What is the expected major organic product from the treatment of 4-methyl-2-pentyne with excess hydrogen in the presence of a platinum catalyst?

A) 4-methylpentane

B) 2-methylpentane

C) 4-methyl-2-pentene

D) 2-methyl-2-pentene

E) 4-methyl-4-pentene

Diff: 2

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

94) What is the expected major organic product from the treatment of 4-methyl-2-pentyne with hydrogen in the presence of Lindlar's catalyst?

A) (E)-4-methyl-2-pentene

B) (E)-4-methyl-2-pentene and (Z)-4-methyl-2-pentene

C) (Z)-4-methyl-2-pentene

D) 2-methylpentane

E) 4-methylpentane

Diff: 2

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

95) What is the expected major organic product from the treatment of 4-methyl-2-pentyne with sodium metal in liquid ammonia?

A) (Z)-4-methyl-2-pentene

B) (E)-2-methyl-4-pentene

C) (Z)-4-methyl-4-pentene

D) (Z)-2methyl-2-pentane

E) (E)-4-methyl-2-pentene

Diff: 2

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

96) In the reaction between an alkyne and Na metal in liquid ammonia, Na acts as an a(n) ________.

A) Brønsted acid

B) Brønsted base

C) reducing agent

D) catalyst

E) electrophile

Diff: 2

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

97) In a dissolving metal reduction of an alkyne, a postulated intermediate is the trans alkenyl radical (shown below). In which orbital type would the unpaired electron be located?

A) sp

B) sp2

C) sp3

D) p

E) s

Diff: 2

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

98) For the reaction shown below, the expected product will have a stereochemistry of ________.

A) only (S)

B) only (R)

C) racemic

D) meso

E) achiral

Diff: 2

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

99) How many distinct eight-carbon hydrocarbon products would be formed in the complete hydrogenation of a mixture of 1-octyne, 2-octyne, and 3-octyne in the presence of a palladium catalyst?

A) 1

B) 2

C) 3

D) 6

E) 8

Diff: 2

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

100) What reagent(s) are required to prepare trans-2-heptene from 2-heptyne?

A) H2, Lindlar's catalyst

B) Na, NH3(l)

C) H2, Pt

D) Cl2, CCl4

E) O3, H2O

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

101) What reagent(s) are needed to accomplish the synthesis shown?

A) H2, Lindlar's catalyst

B) Na, NH3(l)

C) H2, Pt

D) Cl2, CCl4

E) O3, H2O

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

102) Determine which compound will react with sodium in liquid ammonia to form trans-3-hexene.

A) cis-3-hexene

B) trans-2-hexene

C) 3-hexyne

D) 2-hexyne

E) cis-2-hexene

Diff: 1

Learning Objective: 9.5 Discuss methods for reduction of alkynes to alkenes and alkanes

103) Which of the compounds shown below would be the most likely product expected from the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

104) Identify the expected major product from the treatment of 1-pentyne with 1 equivalent of HBr.

A) 1-bromo-1-pentene

B) 2-bromo-1-pentene

C) 1,1-dibromopentane

D) 2,2-dibromopentane

E) 1,2-dibromopentane

Diff: 1

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

105) Identify the expected major product from the treatment of 1-pentyne with 2 equivalents of HBr.

A) 1-bromo-1-pentene

B) 2-bromo-1-pentene

C) 1,1-dibromopentane

D) 2,2-dibromopentane

E) 1,2-dibromopentane

Diff: 1

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

106) Select the structure of the expected major organic product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

107) What is the major expected product(s) of the reaction shown?

A) 2,2-dichloropentane

B) 3,3-dichloropentane

C) 2,3-dichloropentane

D) A and B

E) B and C

Diff: 2

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

108) What is the expected major organic product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

109) Which of the compounds shown would be the most likely product expected from the given reaction?

A) I and II

B) III and IV

C) II and III

D) II and IV

E) I and IV

Diff: 2

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

110) Select the expected major product(s) from the treatment of 1-pentyne with 1equivalent of HBr in the presence of peroxides.

A) 2-bromo-1-pentene

B) (E)-1-bromo-1-pentene

C) (Z)-1-bromo-1-pentene

D) A and B

E) B and C

Diff: 2

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

111) What mechanistic intermediate is used to explain the preference for addition of the Br atom, of HBr, to the internal carbon of a terminal alkyne?

A) Formation of an intermediate with partial positive charge on a primary carbon

B) Formation of an intermediate with partial positive charge on a secondary carbon

C) Addition of the H atom to the carbon already with an H.

D) Addition of H, from HBr, to the least hindered carbon.

E) Steric hindrance for the approach of the Br atom to the primary carbon.

Diff: 2

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

112) How would the expected major organic product(s) from the reaction shown be affected if ROOR were not added?

A) Markovnikov addition would occur.

B) The location of addition of Br would be unpredictable.

C) Heat would need to be added for the reaction to proceed.

D) The reaction would not proceed.

E) The reaction would yield an alkene with two Br substituents.

Diff: 2

Learning Objective: 9.6 Describe the hydrohalogenation of alkynes, including mechanisms and products

113) Identify the best reagent(s) to accomplish the reaction shown.

A) H2SO4, HgSO4, H2O

B) 1. Disiamylborane; 2. HO—, H2O2

C) K2Cr2O7, H+

D) NaOCl

E) NaOH

Diff: 1

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

114) Identify the best reagent(s) to accomplish the reaction shown.

A) H2SO4, HgSO4, H2O

B) 1. Disiamylborane; 2. HO—, H2O2

C) K2Cr2O7, H+

D) NaOCl

E) NaOH

Diff: 1

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

115) What is the expected major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

116) What is the expected major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

117) What is the expected major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

118) What is the expected major product of the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

119) What is the expected final product of the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

120) What is the expected final product of the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

121) For the reaction shown, which of the compounds listed would be the expected enol intermediate?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

122) For the reaction shown, which of the compounds below would be the expected enol intermediate?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

123) Which of the ketones below could not be prepared by an acid-catalyzed hydration of an alkyne?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

124) Which of the following reactions involve an enol intermediate?

A) Hydroboration/oxidation

B) HgSO4 catalyzed hydration in dilute H2SO4

C) Hydrohalogenation

D) A and B

E) A and C

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

125) Which of the following alkynes is expected to produce a single ketone in an acid-catalyzed hydration?

A) 2-decyne

B) 3-decyne

C) 4-decyne

D) 5-decyne

E) All of the above will give a single product

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

126) Which of the following alkynes gives a single ketone in an acid-catalyzed hydration?

A) 2-pentyne

B) 2-hexyne

C) 2-heptyne

D) 3-hexyne

E) 3-heptyne

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

127) How many different organic products would be expected from the reaction below?

A) one

B) two

C) three

D) four

E) five

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

128) Which of the following alkynes would give a single product under hydroboration-oxidation conditions?

A) 1-hexyne

B) 2-hexyne

C) 3-hexyne

D) A and B would each give a single product

E) A and C would each give a single product

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

129) Which of the alkynes below, after undergoing an acid-catalyzed hydration, would be expected to produce two different ketones in nearly equivalent yields?

A) 1-hexyne

B) 2-hexyne

C) 3-hexyne

D) 3-methyl-1-pentyne

E) 4-methyl-1-pentyne

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

130) For the reaction shown, which of the compounds listed below would be the expected major, and final, organic product?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

131) For the reaction below, which of the alkynes listed would be expected to produce the product shown under the given conditions?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

132) What functional group would be expected to be present in the final product of the reaction between 1-hexyne and a mixture of mercuric sulfate and aqueous sulfuric acid?

A) aldehyde

B) ketone

C) diol

D) ether

E) carboxylic acid

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

133) What functional group would be expected to be present in the final product of the reaction shown?

A) aldehyde

B) ketone

C) diol

D) enol

E) alkene

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

134) Which functional group is expected to be produced when cyclodecyne is reacted with disiamylborane, followed by treatment of basic hydrogen peroxide?

A) aldehyde

B) ketone

C) diol

D) ether

E) carboxylic acid

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

135) Which of the reagents below, when reacting with a terminal alkyne, would be expected to produce a ketone as the final major organic product?

A) I and II

B) II

C) III and IV

D) I, II and IV

E) I, III and IV

Diff: 2

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

136) Provide the structure(s) of the expected major organic product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.7 Discuss the acid-catalyzed hydration and the hydroboration-oxidation of alkynes

137) What is the major product of the reaction shown?

A) (E)-2,3-dichloro-2-hexene

B) (Z)-2,3-dichloro-2-hexene

C) 2,2-dichlorohexane

D) 3,3-dichlorohexane

E) 2,2,3,3-tetrachlorohexane

Diff: 1

Learning Objective: 9.8 Describe the halogenation of alkynes, including its products

138) What is the expected major product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.8 Describe the halogenation of alkynes, including its products

139) Identify the expected major product for the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.8 Describe the halogenation of alkynes, including its products

140) What is the expected major product for the following reaction?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.8 Describe the halogenation of alkynes, including its products

141) What is the structure of the expected major product for the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 9.8 Describe the halogenation of alkynes, including its products

142) What is the expected major product(s) of the treatment of 1-pentyne with 1equivalent of Br2?

A) 1,1-dibromo-1-pentene

B) (E)-1,2-dibromo-1-pentene

C) (Z)-1-bromo-1-pentene

D) A and B

E) B and C

Diff: 1

Learning Objective: 9.8 Describe the halogenation of alkynes, including its products

143) Which of the following conditions effectively cleaves all three bonds of a carbon-carbon triple bond?

A) HgSO4 and aqueous H2SO4

B) 1. Disiamylborane; 2. H2O2, NaOH

C) H2, Lindlar's catalyst

D) 1. O3; 2. H2O

E) Na, NH3(l)

Diff: 1

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

144) Predict the major organic products of the reaction shown.

A) I and II

B) II and III

C) I and IV

D) II and IV

E) I and III

Diff: 1

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

145) What are the expected major products of the reaction sequence shown?

A) I and II

B) I, III, and V

C) II, III, and IV

D) I and IV

E) II, III, IV

Diff: 1

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

146) What is the expected major product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

147) How many moles of CO2 are expected to be produced by ozonolysis of one mole of the compound shown?

A) 1

B) 2

C) 3

D) 4

E) 8

Diff: 1

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

148) Which of the alkynes shown would not produce carbon dioxide and a carboxylic acid as the final products upon treatment with ozone followed by water?

A) ethyne

B) propyne

C) 1-butyne

D) 1-pentyne

E) 1-hexyne

Diff: 2

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

149) Which of the following alkynes would be expected to produce only one major organic product through ozonolysis?

A) 1-hexyne

B) 2-hexyne

C) 3-hexyne

D) 2-heptyne

E) 3-heptyne

Diff: 3

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

150) Provide the IUPAC name for the alkyne that would be expected to produce the two compounds listed below through ozonolysis.

CH3CH2CO2H and (CH3)3CCO2H

A) 1-tert-butyl-1-butyne

B) 2,2-dimethyl-3-hexyne

C) 3,3-dimethyl-2-hexyne

D) 5,5-dimethyl-3-hexyne

E) 3-octyne

Diff: 3

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

151) Which alkyne would produce the products below through ozonolysis?

A) HC≡CC≡CCH2C≡CH

B) HC≡CCH2CH2CH2C≡CH

C) CH3C≡CCH2C≡CCH3

D) HC≡CCH2CH2C≡CCH3

E) CH3C≡CC≡CC≡CH

Diff: 3

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

152) What is/are the structure(s) of the expected major organic product(s) of the following reaction?

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 1

Learning Objective: 9.9 Describe the ozonolysis of alkynes, including its products

153) What is the IUPAC name for the expected product of the reaction shown?

A) propyne

B) 1-hexyne

C) 2-hexyne

D) 3-hexyne

E) (E)-3-hexyne

Diff: 1

Learning Objective: 9.10 Describe the alkylation of terminal alkynes

154) What is the IUPAC name for the expected final product of the reaction shown?

A) 5-decyne

B) 3-hexyne

C) 1-octyne

D) 3-octyne

E) 5-octyne

Diff: 1

Learning Objective: 9.10 Describe the alkylation of terminal alkynes

155) What is the expected major final product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 9.10 Describe the alkylation of terminal alkynes

156) What is the expected major final product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) None of the shown products will be produced.

Diff: 2

Learning Objective: 9.10 Describe the alkylation of terminal alkynes

157) What is the expected major product of the reaction sequence shown?

HC≡C:— + (CH3)2CHCH2Br → ?

A) CH≡CH + (CH3)2CHC≡CH

B) (CH3)2CHC≡CCH3

C) (CH3)2CHCH2C≡CH

D) (CH3)2CHCHBrC≡CH

E) CH3CHCH2C≡CCH3

Diff: 2

Learning Objective: 9.10 Describe the alkylation of terminal alkynes

158) Which of the alkyl bromides listed would work as the alkyl halide in step 2 of the reaction sequence shown?

A) I and III

B) II and IV

C) III, IV, V

D) I, II, IV

E) II, III, V

Diff: 3

Learning Objective: 9.10 Describe the alkylation of terminal alkynes

159) Why would the following reaction sequence not produce the expected product shown?

A) NaNH2 is used in the reduction of alkynes to trans alkenes.

B) The secondary alkyl halide would undergo an elimination reaction.

C) Br is not a good enough leaving group.

D) The terminal alkyne is not acidic enough to be deprotonated.

E) The reaction sequence is correct and will produce the shown product.

Diff: 3

Learning Objective: 9.10 Describe the alkylation of terminal alkynes

160) What would be the final major product predicted from the reaction below?

treated with 1. NaNH2, 2. (CH3)2CHCH2Br, 3. Na, NH3(l), 4. xs NaNH2, 5.H2O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

161) Which series of reactions would convert an internal alkene into an internal alkyne?

A) 1. Br2; 2. H2O; 3. Na, NH3 (l),

B) 1. CH3BH; 2. H2O2, NaOH

C) 1. Br2; 2. xs NaNH2; 3. H2O

D) 1. HBr; 2. ROOR; 3. H2O

E) 1. CCl4; 2. H2O; 3. Br2

Diff: 1

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

162) Which of the following methods would be expected to efficiently produce a terminal alkyne from cis-2-butene?

A) 1. H2, Pt; 2. Br2; 3. NaNH2

B) 1. Br2, H2O; 2. 1 equivalent of NaNH2

C) 1. Br2, CCl4; 2. xs NaNH2; 3.H2O

D) 1, CH3CH2MgBr; 2. NaNH2

E) 1. HBr; 2. ROOR

Diff: 1

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

163) Which sequence of reagents would be expected to accomplish the synthesis shown?

A) 1. HBr; 2. 2 NaNH2

B) 1. Br2, CCl4; 2. NaNH2

C) 1. Br2, H2O; 2. NaNH2

D) 1. HBr/ROOR; 2. excess NaNH2

E) 1. Na, NH3(l)

Diff: 2

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

164) To synthesize 3-octyne, you could use bromination and elimination from an intermediate created using which of the following sequences of reactions?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

165) Which sequence of reactions is expected to produce the product shown as the final, and major, organic product?

A) Product I plus 1. H2, Pt; 2. Br2; 3. NaNH2

B) Product II plus 1. Br2, H2O; 2. 1 equivalent of NaNH2

C) Product I plus 1. Br2, CCl4; 2. xs NaNH2, H2O

D) Product III plus 1, CH3CH2MgBr; 2. NaNH2

E) Product IV plus 1. HBr; 2. ROOR

Diff: 3

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

166) Which of the following can successfully be used to synthesize an alkyne?

A) A vicinyl or geminal dihalide that undergoes a series of two elimination reactions

B) A terminal alkyl halide that undergoes a reaction with MCPBA and H3O+

C) A terminal alkyl halide that is treated with NaNH2 and H2O.

D) A terminal alkene that is treated with HBr followed by KOH.

E) A vicinyl or geminal dihalide that is treated with Lindlar's catalyst followed by a strong acid.

Diff: 2

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

167) What product would you expect if you treated the reactant below with two equivalents of NaNH2?

A) A terminal alkyne on the side chain.

B) An internal alkyne on the side chain

C) An alkyne within the ring

D) An alkene within the ring

E) An alkene on the side chain with inversion of configuration

Diff: 3

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

168) Which sequence of reactions is expected to produce the product below as the final, and major, organic product?

A) 1. HC≡CH, NaNH2; 2. CH3CH2CH2Br; 3. Aqueous H2SO4, HgSO4; 4. Br2, CCl4; 5. NaNH2; 6. H2O

B) 1. CH3C≡CH, NaNH2; 2. CH3CH2Br; 3. Disisamylborane; 4. H2O2, NaOH

C) 1. CH3CH2Br, NaNH2; 2. CH3C≡CH; 3. O3; 4. H2O

D) 1. (CH3)2CHCH2Br, NaNH2; 2. HC≡CH; 3. 9-BBN; 4. H2O2, NaOH; 5. Br2, CCl4

Diff: 2

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

169) What sequence of reactions could be used to carry out the reaction shown?

A) 1. NaNH2; 2. H2O

B) 1. HBr, CCl4; 2. NaNH2; 3. H2O.

C) 1. Br2, light; 2. ; 3. xs NaNH2, 4. H2O

D) 1. NaNH2; 2. ; 3. H2/Lindlar’s catalyst

E) 1. Na, NH3; 2. H2O; 3. CCl4; 4. H2/Pt; 5. xs NaNH2

Diff: 2

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

170) Why would the following synthetic route shown be an unsuccessful approach to synthesize the internal alkyne shown?

A) An E2 reaction will be more likely than an SN2 reaction due to the presence of an alkynide ion.

B) A bromide would be added the final product.

C) An SN2 reaction will be favored and therefore an elimination produce is not expected.

D) The reaction will not form the necessary alkynide anion.

E) An E1 reaction will be more likely than an SN2 reaction due to the tertiary carbon in tert-butyl bromide.

Diff: 2

Learning Objective: 9.11 Describe a method for the conversion of an alkene to an alkyne

171) Draw all constitutional isomers of the molecular formula C6H10 that are internal alkynes.

A) I

B) II and III

C) I, II, and III

D) I and III

E) I, III, and IV

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

172) Which of these structures are examples of constitutional isomers of the molecular formula C6H10 that are terminal alkynes?

A) I and II

B) I, II, and III

C) I, III, and IV

D) I, II, and IV

E) I, II, III, and IV

Diff: 2

Learning Objective: 9.2 Assign an IUPAC (systematic) name to an alkyne and describe the alkyne as internal or terminal

173) Compound X is exposed to excess strong base (excess NaNH2 then H2O) to produce an alkyne (compound Y). Alkyne Y is a terminal alkyne, has a molecular formula of C5H8, and has exactly 4 distinct resonances in the (proton-decoupled) 13C NMR spectrum. Which of the following are possible structures for compound X?

A) I and II

B) II and III

C) III and IV

D) I and IV

Diff: 3

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

174) 1-Pentyne was exposed to strong base (NaNH2. then alkyl halide X, producing an internal alkyne (compound Y). Alkyne Y has exactly 4 distinct resonances in the proton-decoupled 13C NMR spectrum. What are the structures of alkyl halide X and alkyne Y?

A) Alkyl halide X is I and alkyne Y is II

B) Alkyl halide X is II and alkyne Y is III

C) Alkyl halide X is I and alkyne Y is IV

D) Alkyl halide X is II and alkyne Y is IV

E) Alkyle halide X is I and alkyne Y is V

Diff: 3

Learning Objective: 9.1 Describe the structure of alkynes and the nature of their chemical function, explaining how alkynes are named

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