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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

E) A) and B)
F) A) and C)

Correct Answer

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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

E) C) and D)
F) A) and D)

Correct Answer

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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

E) None of the above
F) A) and D)

Correct Answer

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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

E) A) and D)
F) B) and C)

Correct Answer

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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.

E) A) and B)
F) A) and C)

Correct Answer

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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.

E) All of the above
F) A) and B)

Correct Answer

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B

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

E) All of the above
F) B) and C)

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

E) B) and C)
F) A) and D)

Correct Answer

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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

E) B) and D)
F) None of the above

Correct Answer

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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

E) A) and B)
F) B) and C)

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D

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

E) All of the above
F) A) and C)

Correct Answer

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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.

E) All of the above
F) A) and C)

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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.

E) All of the above
F) None of the above

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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

E) All of the above
F) A) and D)

Correct Answer

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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

E) C) and D)
F) None of the above

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.

E) C) and D)
F) None of the above

Correct Answer

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C

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

E) A) and B)
F) A) and C)

Correct Answer

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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

E) B) and C)
F) C) and D)

Correct Answer

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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

E) B) and C)
F) A) and C)

Correct Answer

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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

E) B) and C)
F) None of the above

Correct Answer

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