Question 1

Which of the following statements about nucleophilic aromatic substitution is true?

Accepted Answer

A)  For the addition-elimination pathway, the nucleophile may become attached either at the site bearing the leaving group or at the site bearing the ortho hydrogen atom. 
B)  For the elimination-addition pathway, the nucleophile becomes attached only at the site bearing the leaving group. 
C)  The elimination-addition mechanism is not as common as the addition-elimination mechanism. 
D)  In the addition-elimination mechanism, the aromatic ring first accepts a pair of electrons from a nucleophile to form a cationic intermediate. 
A)  For the addition-elimination pathway, the nucleophile may become attached either at the site bearing the leaving group or at the site bearing the ortho hydrogen atom. 
B)  For the elimination-addition pathway, the nucleophile becomes attached only at the site bearing the leaving group. 
C)  The elimination-addition mechanism is not as common as the addition-elimination mechanism. 
D)  In the addition-elimination mechanism, the aromatic ring first accepts a pair of electrons from a nucleophile to form a cationic intermediate.

Question 2

What is the major organic 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 3

What are the two effects that have to be considered to determine the influence a substituent will have on electrophilic aromatic substitution?

Accepted Answer

A)  Steric and electronic 
B)  Inductive and steric 
C)  Inductive and resonance 
D)  Resonance and electronic 
A)  Steric and electronic 
B)  Inductive and steric 
C)  Inductive and resonance 
D)  Resonance and electronic

Question 4

Rank the following deactivating groups in order of increasing deactivating strength, listing the least deactivating first. $$\begin{array} { c c c c } 
- \mathrm { COOH } & - \mathrm { CHO } & - \mathrm { SO } _ { 3 } \mathrm { H } & - \mathrm { NO } _ { 2 } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

Accepted Answer

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

Question 5

What is the major organic 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 substituents is an ortho, para director?

Accepted Answer

A)  "F1F1F1S1F1F1F10 CHO" 
B)  "F1F1F1S1F1F1F10 COOH" 
C)  "F1F1F1S1F1F1F10 NHCOR" 
D)  "F1F1F1S1F1F1F10 CN" 
A)  "F1F1F1S1F1F1F10 CHO" 
B)  "F1F1F1S1F1F1F10 COOH" 
C)  "F1F1F1S1F1F1F10 NHCOR" 
D)  "F1F1F1S1F1F1F10 CN"

Question 7

Rank the following activating groups in order of decreasing strength of activation, listing the most activating first. $$\begin{array} { c c c c } 
\mathrm { H } _ { 3 } \mathrm { C } - & \left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm {~N} - & \mathrm { CH } _ { 3 } \mathrm { O } - & \text { RCOHN- } \
\text { I } & \text { II } & \text { III } & \text { IV }
\end{array}$$

Accepted Answer

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

Question 8

What is the major organic 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 9

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

Accepted Answer

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

Question 10

What is the major organic 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 11

In addition to the product shown, what other product is formed in the following reaction?

Accepted Answer

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

Exam 18: Electrophilic Aromatic Substitution

Which of the following statements about nucleophilic aromatic substitution is true?

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

What are the two effects that have to be considered to determine the influence a substituent will have on electrophilic aromatic substitution?

Rank the following deactivating groups in order of increasing deactivating strength, listing the least deactivating first. - - - - I II III IV

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

Which of the following substituents is an ortho, para director?

Rank the following activating groups in order of decreasing strength of activation, listing the most activating first. - - - RCOHN- I II III IV

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

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

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

In addition to the product shown, what other product is formed in the following reaction?

Structure and Bonding

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Introduction to Organic Molecules and Functional Groups

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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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