Question 1

In the addition of HBr to 1-butyne, the nucleophile in the first step of the mechanism is:

Accepted Answer

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. 
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. B

Question 2

What is the major product of the following reaction?

Accepted Answer

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 A

Question 3

Give the IUPAC name for the following compound.

Accepted Answer

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 D

Question 4

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

Accepted Answer

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

Question 5

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

Accepted Answer

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

Question 6

Which of the following molecular formulas is consistent with the formula for a molecule containing one alkyne and no other degrees of unsaturation? $$\begin{array} { c c c l } 
\mathrm { C } _ { 10 } \mathrm { H } _ { 20 } & \mathrm { C } _ { 10 } \mathrm { H } _ { 22 } & \mathrm { C } _ { 10 } \mathrm { H } _ { 18 } & \mathrm { C } _ { 10 } \mathrm { H } _ { 19 } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

Accepted Answer

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

Question 7

Which of the following represents an internal alkyne?

Accepted Answer

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

Question 8

Give the IUPAC name for the following compound.

Accepted Answer

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

Question 9

Which of the following represents a terminal alkyne?

Accepted Answer

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

Question 10

In the addition of HBr to 1-butyne, the electrophile in the first step of the mechanism is:

Accepted Answer

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. 
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.

Question 11

Which of the following alkynes is a symmetrical alkyne?

Accepted Answer

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

Question 12

Which of the following statements about alkynes is not true?

Accepted Answer

A)  Alkynes undergo many addition reactions. 
B)  Alkynes are more polarizable than alkenes. 
C)  Both F1F1F1S1F1F1F10 bonds of a C-C triple bond are weaker than a C-C F1F1F1S1F1F1F10 bond. 
D)  The electrons in the F1F1F1S1F1F1F10 bonds of alkynes are more tightly held than those of alkenes. 
A)  Alkynes undergo many addition reactions. 
B)  Alkynes are more polarizable than alkenes. 
C)  Both F1F1F1S1F1F1F10 bonds of a C-C triple bond are weaker than a C-C F1F1F1S1F1F1F10 bond. 
D)  The electrons in the F1F1F1S1F1F1F10 bonds of alkynes are more tightly held than those of alkenes.

Question 13

How many F1F1F1S1F1F1F10 bonds and F1F1F1S1F1F1F10 bonds are present in a triple bond?

Accepted Answer

A)  One F1F1F1S1F1F1F10 bond and one F1F1F1S1F1F1F10 bond. 
B)  One F1F1F1S1F1F1F10 bond and two F1F1F1S1F1F1F10 bonds. 
C)  Two F1F1F1S1F1F1F10 bonds and one F1F1F1S1F1F1F10 bond. 
D)  Two F1F1F1S1F1F1F10 bonds and two F1F1F1S1F1F1F10 bonds. 
A)  One F1F1F1S1F1F1F10 bond and one F1F1F1S1F1F1F10 bond. 
B)  One F1F1F1S1F1F1F10 bond and two F1F1F1S1F1F1F10 bonds. 
C)  Two F1F1F1S1F1F1F10 bonds and one F1F1F1S1F1F1F10 bond. 
D)  Two F1F1F1S1F1F1F10 bonds and two F1F1F1S1F1F1F10 bonds.

Question 14

Which of the following anions is the most basic?

Accepted Answer

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

Question 15

What is the major organic product of the following reaction?

Accepted Answer

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

Question 16

Which of the following statements about tautomers is true?

Accepted Answer

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. 
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.

Question 17

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

Accepted Answer

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

Question 18

What is the major organic product of the following reaction?

Accepted Answer

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

Question 19

Which method would work the best in accomplishing the following transformation?

Accepted Answer

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 
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

Question 20

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

Accepted Answer

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

Exam 11: Alkynes

In the addition of HBr to 1-butyne, the nucleophile in the first step of the mechanism is:

What is the major product of the following reaction?

Give the IUPAC name for the following compound.

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

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

Which of the following represents an internal alkyne?

Give the IUPAC name for the following compound.

Which of the following represents a terminal alkyne?

In the addition of HBr to 1-butyne, the electrophile in the first step of the mechanism is:

Which of the following alkynes is a symmetrical alkyne?

Which of the following statements about alkynes is not true?

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

Which of the following anions is the most basic?

What is the major organic product of the following reaction?

Which of the following statements about tautomers is true?

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

What is the major organic product of the following reaction?

Which method would work the best in accomplishing the following transformation?

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

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

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