Question 1

Give the IUPAC name for the following compound.

Accepted Answer

A) trans-2-Acetylenecyclohexanol 
B) trans-2-Ethynylcyclohexanol 
C) trans-2-Acetylene-1-cyclohexanol 
D) trans-2-Ethylenecyclohexanol 
A) trans-2-Acetylenecyclohexanol 
B) trans-2-Ethynylcyclohexanol 
C) trans-2-Acetylene-1-cyclohexanol 
D) trans-2-Ethylenecyclohexanol B

Question 2

Determine the product of the following reaction.

Accepted Answer

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

Question 3

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 D

Question 4

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 5

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 6

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 7

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 8

What is the major product of the following reaction?

Accepted Answer

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

Question 9

Give the IUPAC name for the following compound.

Accepted Answer

A) 2,5-Dimethyl-3-heptyne 
B) 3,6-Dimethy-4-heptyne 
C) 2,5-Dimethyl-3-octyne 
D) 3,6-Dimethyl-4-octyne 
A) 2,5-Dimethyl-3-heptyne 
B) 3,6-Dimethy-4-heptyne 
C) 2,5-Dimethyl-3-octyne 
D) 3,6-Dimethyl-4-octyne

Question 10

What is the major product of the following reaction?

Accepted Answer

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

Question 11

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 12

What is the major product of the following reaction?

Accepted Answer

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

Question 13

What is the product of the following sequence of reactions?

Accepted Answer

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

Question 14

Which of the following about the physical properties of alkynes is not true?

Accepted Answer

A) Alkynes have low melting and boiling points. 
B) Melting and boiling points increase as the number of carbons increases. 
C) Alkynes are soluble in organic solvents. 
D) Alkynes are soluble in water. 
A) Alkynes have low melting and boiling points. 
B) Melting and boiling points increase as the number of carbons increases. 
C) Alkynes are soluble in organic solvents. 
D) Alkynes are soluble in water.

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 bases cannot deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses.

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 17

Which of the following represents a keto-enol tautomeric pair?

Accepted Answer

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

Question 18

Give the IUPAC name for the following compound.

Accepted Answer

A) 3-sec-Butyl-1,4-octadiyne 
B) 3-Isopropyl-1,5-octadiyne 
C) 3-Isopropyl-1,5-nonadiyne 
D) 3-sec-Butyl-1,4-nonadiyne 
A) 3-sec-Butyl-1,4-octadiyne 
B) 3-Isopropyl-1,5-octadiyne 
C) 3-Isopropyl-1,5-nonadiyne 
D) 3-sec-Butyl-1,4-nonadiyne

Question 19

What is the major 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

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

Accepted Answer

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

Exam 11: Alkynes and Synthesis

Give the IUPAC name for the following compound.

Determine the product of the following reaction.

Which of the following anions is the most basic?

What is the product of the following reaction?

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

What is the major organic product of the following reaction?

What is the major product of the following reaction?

Give the IUPAC name for the following compound.

What is the major product of the following reaction?

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

What is the major product of the following reaction?

What is the product of the following sequence of reactions?

Which of the following about the physical properties of alkynes is not true?

What is the major organic product of the following reaction?

Which of the following bases cannot deprotonate acetylene? You are given the pKa values of the conjugate acids in parentheses.

Which of the following represents a keto-enol tautomeric pair?

Give the IUPAC name for the following compound.

What is the major product of the following reaction?

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

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

Which of the following bases cannot deprotonate acetylene? You are given the pK_a values of the conjugate acids in parentheses.

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