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) I
B) II
C) III
D) IV

2) Which of the following represents a terminal alkyne?

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

3) Which of the following represents an internal alkyne?

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

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4) Which of the following alkynes is a symmetrical alkyne?

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

5) How many degrees of unsaturation are introduced by a triple bond?

A) 0
B) 1
C) 2
D) 3

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.

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.

8) Give the IUPAC name for the following compound.

A) 6,6-Dimethyl-3-octyne
B) 3,3-Dimethyl-3-octyne
C) 3,3-Dimethy-5-octyne
D) 6-Ethyl-6-methyl-3-heptyne

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9) Give the IUPAC name for the following compound.

A) 4,4-Diethyl-1-octyne
B) 4,4-Dipropyl-1-heptyne
C) 4,4-Dipropyl-6-heptyne
D) 4,4-Diethyl-6-octyne

10) Give the IUPAC name for the following compound.

A) 4-Chloro-4-methyl-2-heptyne
B) 3-Chloro-3-methyl-4-heptyne
C) 3-Chloro-3-methyl-4-hexyne
D) 4-Chloro-4-methyl-2-hexyne

11) Give the IUPAC name for the following compound.

A) 3-sec-Butyl-1,4-octadiyne
B) 3-Isopropyl-1,5-octadiyne
C) 3-Isopropyl-1,5-nonadiyne
D) 3-sec-Butyl-1,4-nonadiyne

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12) Give the IUPAC name for the following compound.

A) trans-2-Acetylenecyclohexanol
B) trans-2-Ethynylcyclohexanol
C) trans-2-Acetylene-1-cyclohexanol
D) trans-2-Ethylenecyclohexanol

13) Give the IUPAC name for the following compound.

A) 2,5-Dimethyl-3-heptyne
B) 3,6-Dimethy-4-heptyne
C) 2,5-Dimethyl-3-octyne
D) 3,6-Dimethyl-4-octyne

14) Give the IUPAC name for the following compound.

A) 4-Methyl-4-penten-1-yne
B) 2-Methyl-2-hexen-5-yne
C) 5-Methyl-4-hexen-1-yne
D) 2-Methyl-2-penten-4-yne

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.

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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.

17) What is the product of the following reaction?

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

18) What is the product of the following sequence of reactions?

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

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19) What is the product of the following reaction?

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

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

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.

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22) Which of the indicated hydrogen in the following compounds is the least acidic?

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

23) Which of the indicated hydrogen in the following compounds is the most acidic?

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

24) Rank the following compounds in order of decreasing basicity, putting the most basic first.

A) I > II > III

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

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25) Which of the following anions is the most basic?

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

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

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

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28) What is the major product of the following reaction?

A) Only I
B) Only II
C) Only III
D) I, II, and III

29) What is the reagent required to accomplish the following transformation?

A) SOCl2
B) 2eq. HCl
C) Cl2
D) Br2/CCl4

30) In the addition of HBr to 1-butyne, the electrophile in the first step of the mechanism is
A) 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.

31) In the addition of HBr to 1-butyne, the nucleophile in the first step of the mechanism is
A) 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.

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32) What is (are) the product(s) of the following reaction?

A) Only I
B) Only II
C) Only III
D) I, II, and III

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.

34) What is the relationship between the keto and enol forms of acetone, CH3COCH3?
A) Same compounds
B) Diastereomers
C) Enantiomers
D) Constitutional isomers

35) Which of the following compounds is a tautomer of 2-hexanone?

A) Only I and II
B) Only I and III
C) Only II and III
D) I, II, and III

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36) Which of the following compounds can be an enol tautomer of 1,3-cyclohexandione?

A) Only I and II
B) Only I and III
C) Only II and III
D) I, II, and III

37) Which of the following represents a keto-enol tautomeric pair?

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

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38) What is the major organic product of the following reaction?

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

39) What is the major organic product of the following reaction?

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

40) What is the major organic product of the following reaction?

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

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41) What is the major organic product of the following reaction?

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

42) What is the major organic product of the following reaction?

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

43) What is (are) the major organic product(s) of the following reaction?

A) Only I and II
B) Only II and III
C) Only I and III
D) I, II, and III
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44) Determine the product of the following reaction.

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

45) What is the starting material in the following reaction?

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

46) What is the major product of the following reaction?

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

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47) Give the IUPAC name for the following compound.

A) R-4-bromo-1-pentyne
B) S-4-bromo-1-pentyne
C) R-3-bromo-5-pentyne
D) S-3-bromo-5-pentyne

48) Give the IUPAC name for the following compound.

A) R-1-butyn-3-ol
B) S-1-butyn-3-ol
C) R-3-butyn-1-ol
D) S-3-butyn-1-ol

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49) What is the major product of the following reaction?

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

50) What is the major product of the following reaction?

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

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51) What is the major product of the following reaction sequence?

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

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