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Organic Chemistry, 6e (Smith) Chapter 11 Alkynes
1) Which of the following molecular formulas is consistent with the formula for a molecule containing one alkyne and no other degrees of unsaturation?
A) IB) IIC) IIID) IV
Answer: CDifficulty: 1 EasySection: 11.01Topic: AlkynesBloom's: 2. UnderstandChapter: 11
2) Which of the following represents a terminal alkyne?
A) Only I and IIB) Only II and IIIC) Only I and IIID) Only II and IV
Answer: DDifficulty: 1 EasySection: 11.01Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
3) Which of the following represents an internal alkyne?
A) Only I and IIB) Only I and IIIC) Only II and IVD) Only II and III
Answer: BDifficulty: 1 EasySection: 11.01Topic: AlkynesBloom's: 3. ApplyChapter: 11
4) Which of the following alkynes is a symmetrical alkyne?
A) IB) IIC) IIID) IV
Answer: CDifficulty: 1 EasySection: 11.01Topic: AlkynesBloom's: 3. ApplyChapter: 11
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5) How many degrees of unsaturation are introduced by a triple bond?A) 0B) 1C) 2D) 3
Answer: CDifficulty: 1 EasySection: 11.01Topic: AlkynesBloom's: 5. EvaluateChapter: 11Accessibility: Keyboard Navigation
6) How many s bonds and p bonds are present in a triple bond?A) One s bond and one p bond.B) One s bond and two p bonds.C) Two s bonds and one p bond.D) Two s bonds and two p bonds.
Answer: BDifficulty: 1 EasySection: 11.01Topic: AlkynesBloom's: 3. ApplyChapter: 11Accessibility: Keyboard Navigation
7) Which of the following statements about alkynes is not true?A) Alkynes undergo many addition reactions.B) Alkynes are more polarizable than alkenes.C) Both p bonds of a C-C triple bond are weaker than a C-C s bond.D) The electrons in the p bonds of alkynes are more tightly held than those of alkenes.
Answer: DDifficulty: 1 EasySection: 11.01Topic: AlkynesBloom's: 3. ApplyChapter: 11Accessibility: Keyboard Navigation
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written consent of McGraw-Hill Education.
8) Give the IUPAC name for the following compound.
A) 6,6-Dimethyl-3-octyneB) 3,3-Dimethyl-3-octyneC) 3,3-Dimethy-5-octyneD) 6-Ethyl-6-methyl-3-heptyne
Answer: ADifficulty: 1 EasySection: 11.02Topic: AlkynesBloom's: 3. ApplyChapter: 11
9) Give the IUPAC name for the following compound.
A) 4,4-Diethyl-1-octyneB) 4,4-Dipropyl-1-heptyneC) 4,4-Dipropyl-6-heptyneD) 4,4-Diethyl-6-octyne
Answer: BDifficulty: 2 MediumSection: 11.02Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
10) Give the IUPAC name for the following compound.
A) 4-Chloro-4-methyl-2-heptyneB) 3-Chloro-3-methyl-4-heptyneC) 3-Chloro-3-methyl-4-hexyneD) 4-Chloro-4-methyl-2-hexyne
Answer: DDifficulty: 2 MediumSection: 11.02Topic: AlkynesBloom's: 3. ApplyChapter: 11
11) Give the IUPAC name for the following compound.
A) 3-sec-Butyl-1,4-octadiyneB) 3-Isopropyl-1,5-octadiyneC) 3-Isopropyl-1,5-nonadiyneD) 3-sec-Butyl-1,4-nonadiyne
Answer: BDifficulty: 2 MediumSection: 11.02Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
12) Give the IUPAC name for the following compound.
A) trans-2-AcetylenecyclohexanolB) trans-2-EthynylcyclohexanolC) trans-2-Acetylene-1-cyclohexanolD) trans-2-Ethylenecyclohexanol
Answer: BDifficulty: 2 MediumSection: 11.02Topic: AlkynesBloom's: 3. ApplyChapter: 11
13) Give the IUPAC name for the following compound.
A) 2,5-Dimethyl-3-heptyneB) 3,6-Dimethy-4-heptyneC) 2,5-Dimethyl-3-octyneD) 3,6-Dimethyl-4-octyne
Answer: ADifficulty: 2 MediumSection: 11.02Topic: AlkynesBloom's: 3. ApplyChapter: 11
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14) Give the IUPAC name for the following compound.
A) 4-Methyl-4-penten-1-yneB) 2-Methyl-2-hexen-5-yneC) 5-Methyl-4-hexen-1-yneD) 2-Methyl-2-penten-4-yne
Answer: CDifficulty: 2 MediumSection: 11.02Topic: AlkynesBloom's: 3. ApplyChapter: 11
15) Which of the following about the physical properties of alkynes is not true?A) Alkynes have low melting and boiling points.B) Melting and boiling points increase as the number of carbons increases.C) Alkynes are soluble in organic solvents.D) Alkynes are soluble in water.
Answer: DDifficulty: 1 EasySection: 11.03Topic: AlkynesBloom's: 3. ApplyChapter: 11Accessibility: Keyboard Navigation
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written consent of McGraw-Hill Education.
16) Which of the following explains why 1-pentyne has a slightly higher boiling point than 1-pentene?A) 1-Pentyne has more carbons than 1-pentene.B) 1-Pentyne has more carbons per hydrogen than 1-pentene.C) 1-Pentyne is linear while 1-pentene is trigonal planar.D) The C-C triple bond in 1-pentyne is more polar than the C-C double bond in 1-pentene.
Answer: DDifficulty: 1 EasySection: 11.03Topic: AlkynesBloom's: 3. ApplyChapter: 11Accessibility: Keyboard Navigation
17) What is the product of the following reaction?
A) IB) IIC) IIID) IV
Answer: BDifficulty: 1 EasySection: 11.05Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
18) What is the product of the following sequence of reactions?
A) IB) IIC) IIID) IV
Answer: BDifficulty: 1 EasySection: 11.05Topic: AlkynesBloom's: 3. ApplyChapter: 11
19) What is the product of the following reaction?
A) IB) IIC) IIID) IV
Answer: ADifficulty: 1 EasySection: 11.05Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
20) Which method would work the best in accomplishing the following transformation?
A) [1] HBr; [2] 2eq. NaNH2
B) [1] Br2; [2] 2eq. NaNH2
C) [1] Br2, H2O; [2] NaNH2
D) [1]BH3, THF; [2] H2O2, NaOH; [3] NaNH2
Answer: BDifficulty: 2 MediumSection: 11.05Topic: AlkynesBloom's: 3. ApplyChapter: 11
21) Which of the following statements about the reactions of alkynes is not true?A) Alkynes contain easily broken p bonds.B) Alkynes undergo addition reactions.C) When alkynes undergo two sequential addition reactions, four new s bonds are formed.D) When alkynes undergo two sequential addition reactions, two new s bonds and a p bond are formed.
Answer: DDifficulty: 1 EasySection: 11.06Topic: AlkynesBloom's: 3. ApplyChapter: 11Accessibility: Keyboard Navigation
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22) Which of the indicated hydrogen in the following compounds is the least acidic?
A) IB) IIC) IIID) IV
Answer: DDifficulty: 1 EasySection: 11.06Topic: AlkynesBloom's: 3. ApplyChapter: 11
23) Which of the indicated hydrogen in the following compounds is the most acidic?
A) IB) IIC) IIID) IV
Answer: CDifficulty: 1 EasySection: 11.06Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
24) Rank the following compounds in order of decreasing basicity, putting the most basic first.
A) I > II > IIIB) III > II > IC) III > I > IID) II > III > I
Answer: BDifficulty: 2 MediumSection: 11.06Topic: AlkynesBloom's: 3. ApplyChapter: 11
25) Which of the following anions is the most basic?
A) IB) IIC) IIID) IV
Answer: DDifficulty: 1 EasySection: 11.06Topic: AlkynesBloom's: 3. ApplyChapter: 11
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26) Which of the following bases can deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses.
A) Only I and IIB) Only I and IIIC) Only II and IIID) Only II and IV
Answer: BDifficulty: 1 EasySection: 11.06Topic: AlkynesBloom's: 3. ApplyChapter: 11
27) Which of the following bases cannot deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses.
A) Only I and IIB) Only I and IIIC) Only II and IIID) Only II and IV
Answer: DDifficulty: 1 EasySection: 11.06Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
28) What is the major product of the following reaction?
A) Only IB) Only IIC) Only IIID) I, II, and III
Answer: ADifficulty: 1 EasySection: 11.07Topic: AlkynesBloom's: 3. ApplyChapter: 11
29) What is the reagent required to accomplish the following transformation?
A) SOCl2B) 2eq. HClC) Cl2D) Br2/CCl4
Answer: BDifficulty: 1 EasySection: 11.07Topic: AlkynesBloom's: 3. ApplyChapter: 11
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30) In the addition of HBr to 1-butyne, the electrophile in the first step of the mechanism isA) the Csp-H1s bond of 1-butyne.B) the C-C triple bond of 1-butyne.C) the H atom in HBr.D) the Br ion.
Answer: CDifficulty: 1 EasySection: 11.07Topic: AlkynesBloom's: 3. ApplyChapter: 11Accessibility: Keyboard Navigation
31) In the addition of HBr to 1-butyne, the nucleophile in the first step of the mechanism isA) the Csp-H1s bond of 1-butyne.B) the C-C triple bond of 1-butyne.C) the H atom in HBr.D) the Br ion.
Answer: BDifficulty: 1 EasySection: 11.07Topic: AlkynesBloom's: 3. ApplyChapter: 11Accessibility: Keyboard Navigation
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written consent of McGraw-Hill Education.
32) What is (are) the product(s) of the following reaction?
A) Only IB) Only IIC) Only IIID) I, II, and III
Answer: ADifficulty: 1 EasySection: 11.08Topic: AlkynesBloom's: 3. ApplyChapter: 11
33) Which of the following statements about tautomers is true?A) Tautomers differ in the position of a single bond and a hydrogen atom.B) Tautomers differ in the position of a double bond and a carbon atom.C) Tautomers differ in the position of a double bond and a hydrogen atom.D) Tautomers differ in the position of a single bond and a carbon atom.
Answer: CDifficulty: 1 EasySection: 11.09Topic: AlkynesBloom's: 3. ApplyChapter: 11Accessibility: Keyboard Navigation
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written consent of McGraw-Hill Education.
34) What is the relationship between the keto and enol forms of acetone, CH3COCH3?A) Same compoundsB) DiastereomersC) EnantiomersD) Constitutional isomers
Answer: DDifficulty: 2 MediumSection: 11.09Topic: AlkynesBloom's: 3. ApplyChapter: 11Accessibility: Keyboard Navigation
35) Which of the following compounds is a tautomer of 2-hexanone?
A) Only I and IIB) Only I and IIIC) Only II and IIID) I, II, and III
Answer: ADifficulty: 1 EasySection: 11.09Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
36) Which of the following compounds can be an enol tautomer of 1,3-cyclohexandione?
A) Only I and IIB) Only I and IIIC) Only II and IIID) I, II, and III
Answer: BDifficulty: 2 MediumSection: 11.09Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
37) Which of the following represents a keto-enol tautomeric pair?
A) IB) IIC) IIID) IV
Answer: DDifficulty: 1 EasySection: 11.09Topic: AlkynesBloom's: 3. ApplyChapter: 11
38) What is the major organic product of the following reaction?
A) IB) IIC) IIID) IV
Answer: CDifficulty: 1 EasySection: 11.09Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
39) What is the major organic product of the following reaction?
A) IB) IIC) IIID) IV
Answer: CDifficulty: 1 EasySection: 11.09Topic: AlkynesBloom's: 3. ApplyChapter: 11
40) What is the major organic product of the following reaction?
A) IB) IIC) IIID) IV
Answer: ADifficulty: 1 EasySection: 11.10Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
41) What is the major organic product of the following reaction?
A) IB) IIC) IIID) IV
Answer: DDifficulty: 1 EasySection: 11.10Topic: AlkynesBloom's: 3. ApplyChapter: 11
42) What is the major organic product of the following reaction?
A) IB) IIC) IIID) IV
Answer: DDifficulty: 1 EasySection: 11.11Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
43) What is (are) the major organic product(s) of the following reaction?
A) Only I and IIB) Only II and IIIC) Only I and IIID) I, II, and III
Answer: ADifficulty: 1 EasySection: 11.11Topic: AlkynesBloom's: 3. ApplyChapter: 11
44) Determine the product of the following reaction.
A) IB) IIC) IIID) IV
Answer: ADifficulty: 2 MediumSection: 11.11Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
45) What is the starting material in the following reaction?
A) IB) IIC) IIID) IV
Answer: ADifficulty: 2 MediumSection: 11.12Topic: AlkynesBloom's: 3. ApplyChapter: 11
46) What is the major product of the following reaction?
A) IB) IIC) IIID) IV
Answer: CDifficulty: 2 MediumSection: 11.12Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
47) Give the IUPAC name for the following compound.
A) R-4-bromo-1-pentyneB) S-4-bromo-1-pentyneC) R-3-bromo-5-pentyneD) S-3-bromo-5-pentyne
Answer: BDifficulty: 2 MediumSection: 11.02Topic: AlkynesBloom's: 3. ApplyChapter: 11
48) Give the IUPAC name for the following compound.
A) R-1-butyn-3-olB) S-1-butyn-3-olC) R-3-butyn-1-olD) S-3-butyn-1-ol
Answer: DDifficulty: 2 MediumSection: 11.02Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
49) What is the major product of the following reaction?
A) IB) IIC) IIID) IV
Answer: CDifficulty: 2 MediumSection: 11.08Topic: AlkynesBloom's: 3. ApplyChapter: 11
25Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior
written consent of McGraw-Hill Education.
50) What is the major product of the following reaction?
A) IB) IIC) IIID) IV
Answer: ADifficulty: 2 MediumSection: 11.10Topic: AlkynesBloom's: 3. ApplyChapter: 11
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written consent of McGraw-Hill Education.
51) What is the major product of the following reaction sequence?
A) IB) IIC) IIID) IV
Answer: CDifficulty: 2 MediumSection: 11.11Topic: AlkynesBloom's: 3. ApplyChapter: 11
27Copyright 2020 © McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior
written consent of McGraw-Hill Education.
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