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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.

Correct Answer

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B

Determine the product of the following reaction. Determine the product of the following reaction. A) I B) II C) III D) IV


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

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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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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.

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Which of the indicated hydrogen in the following compounds is the most acidic? Which of the indicated hydrogen in the following compounds is the most acidic? A) I B) II C) III D) IV


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

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What is the major organic product of the following reaction? What is the major organic product of the following reaction? A) I B) II C) III D) IV


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

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Which of the following anions is the most basic? Which of the following anions is the most basic? A) I B) II C) III D) IV


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

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What is the major organic product of the following reaction? What is the major organic product of the following reaction? A) I B) II C) III D) IV


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

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Which of the following molecular formulas is consistent with the formula for a molecule containing one alkyne and no other degrees of unsaturation? 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


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

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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.

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Which of the following represents a keto-enol tautomeric pair? Which of the following represents a keto-enol tautomeric pair? A) I B) II C) III D) IV


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

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What is the relationship between the keto and enol forms of acetone, CH3COCH3?


A) Same compounds
B) Diastereomers
C) Enantiomers
D) Constitutional isomers

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D

What is the major organic product of the following reaction? What is the major organic product of the following reaction? A) I B) II C) III D) IV


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

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Which of the indicated hydrogen in the following compounds is the least acidic? Which of the indicated hydrogen in the following compounds is the least acidic? A) I B) II C) III D) IV


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

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Which of the following bases can deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses. <sup> </sup>Which of the following bases can deprotonate acetylene? You are given the pK<sub>a</sub> 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


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

Correct Answer

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


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

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


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

Correct Answer

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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.

Correct Answer

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C

Which method would work the best in accomplishing the following transformation? Which method would work the best in accomplishing the following transformation? A) [1] HBr; [2] 2eq.NaNH<sub>2</sub> B) [1] Br<sub>2</sub>; [2] 2eq.NaNH<sub>2</sub> C) [1] Br<sub>2</sub>, H<sub>2</sub>O; [2] NaNH<sub>2</sub> D) [1]BH<sub>3</sub>, THF; [2] H<sub>2</sub>O<sub>2</sub>, NaOH; [3] NaNH<sub>2</sub>


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

Correct Answer

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Which of the following bases cannot deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses. <sup> </sup>Which of the following bases cannot deprotonate acetylene? You are given the pK<sub>a</sub> 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


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

Correct Answer

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