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Which of the following represents an internal alkyne? 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


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

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

Correct Answer

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Give the IUPAC name for the following compound. 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


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

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

Correct Answer

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D

Which of the following bases can deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses. CH3NH−(pKa=40) CO32−(pKa=10.2) CH2=CH−(pKa=44) (CH3) 3CO−(pKa=18) \mathrm { CH } _ { 3 } \mathrm { NH } ^ { - } \left( \mathrm { p } K _ { a } = 40 \right) \quad \mathrm { CO } _ { 3 } ^ { 2 - } \left( \mathrm { p } K _ { a } = 10.2 \right) \quad \mathrm { CH } _ { 2 } = \mathrm { CH } ^ { - } \left( \mathrm { p } K _ { a } = 44 \right) \quad \left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CO } ^ { - } \left( \mathrm { p } K _ { a } = 18 \right) I \quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad II \quad\quad\quad\quad\quad\quad\quad\quad\quad III \quad\quad\quad\quad\quad\quad\quad\quad\quad\quad\quad IV


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

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

Correct Answer

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Which of the following alkynes is a symmetrical alkyne? Which of the following alkynes is a symmetrical alkyne? 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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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) None of the above
F) A) and B)

Correct Answer

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

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) A) and B)
F) None of the above

Correct Answer

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How many bonds and bonds are present in a triple bond?


A) One bond and one bond.
B) One bond and two bonds.
C) Two bonds and one bond.
D) Two bonds and two bonds.

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

Correct Answer

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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) C) and D)

Correct Answer

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


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

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

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 bonds of a C-C triple bond are weaker than a C-C bond.
D) The electrons in the bonds of alkynes are more tightly held than those of alkenes.

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

Correct Answer

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Which of the following compounds is a tautomer of 2-hexanone? 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, III


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

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

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

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) A) and C)

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? C10H20C10H22C10H18C10H19 I  II  III  IV \begin{array} { c c c l } \mathrm { C } _ { 10 } \mathrm { H } _ { 20 } & \mathrm { C } _ { 10 } \mathrm { H } _ { 22 } & \mathrm { C } _ { 10 } \mathrm { H } _ { 18 } & \mathrm { C } _ { 10 } \mathrm { H } _ { 19 } \\\text { I } & \text { II } & \text { III } & \text { IV }\end{array}


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

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

Correct Answer

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Which of the following represents a terminal alkyne? 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


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

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

Correct Answer

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Give the IUPAC name for the following compound. 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


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

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

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

Correct Answer

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


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

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

Correct Answer

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A

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