Question 1

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 2

Which of the following is the most reactive substrate in an E1 reaction?

Accepted Answer

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

Question 3

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 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

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 6

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 7

Which of the following is most likely to react as a nucleophile rather than a base? $$\begin{array} { c c c c } 
\mathrm { KOC } \left( \mathrm { CH } _ { 3 } \right) _ { 3 } & \mathrm { CH } _ { 3 } \mathrm { COO } ^ { - } & \mathrm { DBU } & \mathrm { DBN } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

Accepted Answer

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

Question 8

What is (are) the elimination 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 9

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 10

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 11

Which of the following represents the rate law for an E2 reaction?

Accepted Answer

A)  Rate = k[alkyl halide] 
B)  Rate = k[alkyl halide][base] 
C)  Rate = k[alkyl halide]2 
D)  Rate = k[base]2 
A)  Rate = k[alkyl halide] 
B)  Rate = k[alkyl halide][base] 
C)  Rate = k[alkyl halide]2 
D)  Rate = k[base]2

Question 12

What is the major elimination product in the reaction of 1-bromobutane with potassium tert-butoxide in tert-butanol?

Accepted Answer

A)  cis-2-Butene 
B)  1-Butene 
C)  trans-2-Butene 
D)  Butanol 
A)  cis-2-Butene 
B)  1-Butene 
C)  trans-2-Butene 
D)  Butanol

Question 13

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 14

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 15

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 16

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 17

Consider the following E2 reaction. What rate equation would be observed for this reaction? $$\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { Br } + \stackrel { \oplus \ominus  } { \mathrm { KOC } } \left( \mathrm { CH } _ { 2 } \right) _ { 3 } \longrightarrow \mathrm { CH } _ { 3 } \mathrm { CH } = \mathrm { CH } _ { 2 } + \mathrm { KBr } ^ { + }$$

Accepted Answer

A)  Rate = k[CH3CH2CH2Br] 
B)  Rate = k[CH3CH2CH2Br][KOC(CH3)3] 
C)  Rate = k[CH3CH2CH2Br][KOC(CH3)3]2 
D)  Rate = k[CH3CH2CH2Br]2[KOC(CH3)3] 
A)  Rate = k[CH3CH2CH2Br] 
B)  Rate = k[CH3CH2CH2Br][KOC(CH3)3] 
C)  Rate = k[CH3CH2CH2Br][KOC(CH3)3]2 
D)  Rate = k[CH3CH2CH2Br]2[KOC(CH3)3]

Question 18

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 19

Which of the following is the major elimination 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 product of the following reaction?

Accepted Answer

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

Exam 8: Alkyl Halides and Elimination Reactions

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

Which of the following is the most reactive substrate in an E1 reaction?

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

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

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

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

Which of the following is most likely to react as a nucleophile rather than a base? I II III IV

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

What is the product of the following reaction?

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

Which of the following represents the rate law for an E2 reaction?

What is the major elimination product in the reaction of 1-bromobutane with potassium tert-butoxide in tert-butanol?

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

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

What is the product of the following reaction?

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

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

Which of the following is the major elimination product of the following reaction?

What is the product of the following reaction?

Structure and Bonding

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Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

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Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

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Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

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Carbon-Carbon Bond Forming Reactions in Organic Synthesis

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