Question 1

Give the IUPAC name for the following compound.

Accepted Answer

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

Question 2

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

Question 3

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 4

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 5

Give the IUPAC name for the following compound.

Accepted Answer

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 
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

Question 6

What is the major product of the following reaction sequence?

Accepted Answer

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

Question 7

Give the IUPAC name for the following compound.

Accepted Answer

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

Question 8

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

Accepted Answer

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

Question 9

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 10

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 11

Which of the following statements about the reactions of alkynes is not true?

Accepted Answer

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. 
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.

Question 12

What is the starting material in the following reaction?

Accepted Answer

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

Question 13

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.

Question 14

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

Accepted Answer

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

Question 15

Which of the following explains why 1-pentyne has a slightly higher boiling point than 1-pentene?

Accepted Answer

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. 
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.

Question 16

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 17

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 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. 
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.

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

What is the product of the following reaction?

Accepted Answer

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

Question 20

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

Exam 11: Alkynes and Synthesis

Give the IUPAC name for the following compound.

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

What is the major organic product of the following reaction?

What is the major organic product of the following reaction?

Give the IUPAC name for the following compound.

What is the major product of the following reaction sequence?

Give the IUPAC name for the following compound.

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

Give the IUPAC name for the following compound.

Which of the following statements about tautomers is true?

Which of the following statements about the reactions of alkynes is not true?

What is the starting material in the following reaction?

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

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

Which of the following explains why 1-pentyne has a slightly higher boiling point than 1-pentene?

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

Which of the following statements about alkynes is not true?

What is the major organic product of the following reaction?

What is the product of the following reaction?

Give the IUPAC name for the following compound.

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 Related Compounds

Alkenes and Addition Reactions

Oxidation and Reduction

Radical Reactions

Conjugation,resonance,and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters