Question 1

What is (are) the product(s) of the following reaction?

Accepted Answer

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

Question 2

Which of the following alkenes is the most stable?

Accepted Answer

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

Question 3

What is (are) the product(s) of the following reaction?

Accepted Answer

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

Question 4

What is the major elimination product obtained from 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 is the dihalide that can be used to prepare the alkyne below?

Accepted Answer

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

Question 6

Which of the following is the dihalide that can be used to prepare the alkyne below?

Accepted Answer

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

Question 7

What is (are) the product(s) of the following reaction?

Accepted Answer

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

Question 8

Which of the following statements about the mechanism of an E2 reaction is true?

Accepted Answer

A) All bonds are broken and formed in multiple steps. 
B) The reaction is not concerted. 
C) Entropy favors the reactants of an E2 reaction. 
D) Entropy favors the products of an E2 reaction. 
A) All bonds are broken and formed in multiple steps. 
B) The reaction is not concerted. 
C) Entropy favors the reactants of an E2 reaction. 
D) Entropy favors the products of an E2 reaction.

Question 9

Which of the following alkyl halide reacts the fastest in an E2 reaction?

Accepted Answer

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

Question 10

Which of the following is the least reactive substrate in an E2 reaction?

Accepted Answer

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

Question 11

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 12

What is the major elimination product obtained from the following reaction?

Accepted Answer

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

Question 13

How many different E2 products can form from the dehydrohalogenation of 2-bromobutane?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 4 
A) 1 
B) 2 
C) 3 
D) 4

Question 14

Which of the following statements about an E1 mechanism is true?

Accepted Answer

A) The identity of the leaving group affects the rate of reaction. 
B) The reaction follows second-order kinetics. 
C) The reaction is slowest with tertiary substrates. 
D) Polar aprotic solvents favor the E1 mechanism. 
A) The identity of the leaving group affects the rate of reaction. 
B) The reaction follows second-order kinetics. 
C) The reaction is slowest with tertiary substrates. 
D) Polar aprotic solvents favor the E1 mechanism.

Question 15

Classify each alkene in vitamin D3 labeled I, II, III by the number of carbon substituents bonded to the double bond.

Accepted Answer

A) I = Disubstituted; II = trisubstituted; III = trisubstituted. 
B) I = Monosubstituted; II = disubstituted; III = trisubstituted. 
C) I = Disubstituted; II = disubstituted; III = trisubstituted. 
D) I = Disubstituted; II = trisubstituted; III = disubstituted. 
A) I = Disubstituted; II = trisubstituted; III = trisubstituted. 
B) I = Monosubstituted; II = disubstituted; III = trisubstituted. 
C) I = Disubstituted; II = disubstituted; III = trisubstituted. 
D) I = Disubstituted; II = trisubstituted; III = disubstituted.

Question 16

Which of the following statements about an E1 mechanism is not true?

Accepted Answer

A) It is a two-step process and has the same first step as an SN1 mechanism. 
B) It involves the formation of a carbocation from eliminating a good leaving group. 
C) A common competing reaction is rearrangement of a less stable carbocation to a more stable carbocation. 
D) The loss of a proton by the carbocation is a slow step. 
A) It is a two-step process and has the same first step as an SN1 mechanism. 
B) It involves the formation of a carbocation from eliminating a good leaving group. 
C) A common competing reaction is rearrangement of a less stable carbocation to a more stable carbocation. 
D) The loss of a proton by the carbocation is a slow step.

Question 17

Which of the labeled protons in the compound below is most readily abstracted under E2 conditions?

Accepted Answer

A) Ha 
B) Hb 
C) Hc 
D) Hd 
A) Ha 
B) Hb 
C) Hc 
D) Hd

Question 18

Which of the following alkyl chloride affords alkene A exclusively under E2 reaction condition?

Accepted Answer

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

Question 19

Which of the following statements about an E1 mechanism is not true?

Accepted Answer

A) The reaction is fastest with tertiary alkyl halides. 
B) A better leaving group makes the reaction rate increase. 
C) The reaction follows first-order kinetics. 
D) Stronger bases favor the E1 reaction. 
A) The reaction is fastest with tertiary alkyl halides. 
B) A better leaving group makes the reaction rate increase. 
C) The reaction follows first-order kinetics. 
D) Stronger bases favor the E1 reaction.

Question 20

What is the most likely mechanism for the reaction below?

Accepted Answer

A) SN1 
B) SN2 
C) E1 
D) E2 
A) SN1 
B) SN2 
C) E1 
D) E2

Exam 8: Alkyl Halides and Elimination Reactions

What is (are) the product(s) of the following reaction?

Which of the following alkenes is the most stable?

What is (are) the product(s) of the following reaction?

What is the major elimination product obtained from the following reaction?

Which of the following is the dihalide that can be used to prepare the alkyne below?

Which of the following is the dihalide that can be used to prepare the alkyne below?

What is (are) the product(s) of the following reaction?

Which of the following statements about the mechanism of an E2 reaction is true?

Which of the following alkyl halide reacts the fastest in an E2 reaction?

Which of the following is the least reactive substrate in an E2 reaction?

What is the product of the following reaction?

What is the major elimination product obtained from the following reaction?

How many different E2 products can form from the dehydrohalogenation of 2-bromobutane?

Which of the following statements about an E1 mechanism is true?

Classify each alkene in vitamin D3 labeled I, II, III by the number of carbon substituents bonded to the double bond.

Which of the following statements about an E1 mechanism is not true?

Which of the labeled protons in the compound below is most readily abstracted under E2 conditions?

Which of the following alkyl chloride affords alkene A exclusively under E2 reaction condition?

Which of the following statements about an E1 mechanism is not true?

What is the most likely mechanism for the reaction below?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alcohols, Ethers, and Related Compounds

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

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

Synthetic Polymers

Lipids

Filters

Classify each alkene in vitamin D₃ labeled I, II, III by the number of carbon substituents bonded to the double bond.