Exam 25: Electrophilic Aromatic Substitution 2: Substitution on Mono- and Disubstituted Benzene and Other Aromatic Rings

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Which of the following could undergo a nucleophilic aromatic substitution via addition-elimination?

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Question 1

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Fill in the necessary reagent and solvent to carry out the reaction below.

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Question 2

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Which of the following would produce a mixture of two isomers as the major products when allowed to react with Cl₂ and AlCl₃?

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Question 3

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Fill in the missing starting material for the synthesis below.

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Question 4

Which of the following statements is true regarding the two reactions shown below?

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Question 5

Fill in the missing reagents to carry out the synthesis below.

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Question 6

Which of the following resonance structures is least stable?

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Question 7

Predict the major product(s)of the reaction below,and draw three resonance structures for the intermediate that is formed.

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Question 8

Rank the following from slowest to fastest rate of nitration.

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Question 9

Fill in the intermediates and reagents to complete the synthetic scheme below.

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Question 10

Which of the following would be a major product of the reaction below?

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Question 11

Draw the mechanism for the reaction below.Label each elementary step.

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Question 12

What is the major product of the following sequence of reactions?

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Question 13

An amine substituent will coordinate to a Lewis acid such as AlCl₃,thereby deactivating the benzene ring.If the amine is converted to an amide,however,this coordination does not take place.Briefly explain why this is so,using a resonance structure to illustrate your answer.

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Question 14

Show how you would synthesize the compound below from benzene.

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Question 15

Draw all possible isomers that could be formed in the reaction below,and predict the major product.

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Question 16

Predict the major product of the reaction below.

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Question 17

Draw a complete,detailed mechanism for the reaction below.Label each elementary step,and indicate the rate-determining step.

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Question 18

Which of the following arenium ions is most stable?

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Question 19

How many of the following molecules will undergo chlorination at a higher rate than benzene and will produce ortho/para-substituted products?

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Question 20

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Exam 25: Electrophilic Aromatic Substitution 2: Substitution on Mono- and Disubstituted Benzene and Other Aromatic Rings

Which of the following could undergo a nucleophilic aromatic substitution via addition-elimination?

Fill in the necessary reagent and solvent to carry out the reaction below.

Which of the following would produce a mixture of two isomers as the major products when allowed to react with Cl2 and AlCl3?

Fill in the missing starting material for the synthesis below.

Which of the following statements is true regarding the two reactions shown below?

Fill in the missing reagents to carry out the synthesis below.

Which of the following resonance structures is least stable?

Predict the major product(s)of the reaction below,and draw three resonance structures for the intermediate that is formed.

Rank the following from slowest to fastest rate of nitration.

Fill in the intermediates and reagents to complete the synthetic scheme below.

Which of the following would be a major product of the reaction below?

Draw the mechanism for the reaction below.Label each elementary step.

What is the major product of the following sequence of reactions?

An amine substituent will coordinate to a Lewis acid such as AlCl3,thereby deactivating the benzene ring.If the amine is converted to an amide,however,this coordination does not take place.Briefly explain why this is so,using a resonance structure to illustrate your answer.

Show how you would synthesize the compound below from benzene.

Draw all possible isomers that could be formed in the reaction below,and predict the major product.

Predict the major product of the reaction below.

Draw a complete,detailed mechanism for the reaction below.Label each elementary step,and indicate the rate-determining step.

Which of the following arenium ions is most stable?

How many of the following molecules will undergo chlorination at a higher rate than benzene and will produce ortho/para-substituted products?

Atomic and Molecular Structure

Interchapter: Nomenclature 1-4

Interchapter 1molecular Orbital Theory and Chemical Reactions

Three-Dimensional Geometry,intermolecular Interactions,and Physical Properties

Orbital Interactions 1: Hybridization and Two-Center Molecular Orbitals

Isomerism 1: Conformational and Constitutional Isomers

Isomerism 2: Chirality,enantiomers,and Diastereomers

The Proton Transfer Reaction: an Introduction to Mechanisms,thermodynamics,and Charge Stability

An Overview of the Most Common Elementary Steps

An Introduction to Multistep Mechanisms: Sn1 and E1 Reactions

Nucleophilic Substitution and Elimination Reactions 1: Competition Among Sn2,sn1,e2,and E1 Reactions

Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis

Electrophilic Addition to Nonpolar Π Bonds 1: Addition of a Brønsted Acid

Electrophilic Addition to Nonpolar Π Bonds 2: Reactions Involving Cyclic Transition States

Organic Synthesis 1: Beginning Concepts

Orbital Interactions 2: Extended Π Systems,conjugation,and Aromaticity

Structure Determination 1: Ultravioletvisible and Infrared Spectroscopies

Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry

Nucleophilic Addition to Polar Π Bonds 1: Addition of Strong Nucleophiles

Nucleophilic Addition to Polar Π Bonds 2: Addition of Weak Nucleophiles and Acid and Base Catalysis

Organic Synthesis 2: Intermediate Topics in Synthesis Design,and Useful Reduction and Oxidation Reactions

Nucleophilic Additionelimination Reactions 1: the General Mechanism Involving Strong Nucleophiles

Nucleophilic Additionelimination Reactions 2: Weak Nucleophiles

Electrophilic Aromatic Substitution 1: Substitution on Benzene; Useful Accompanying Reactions

The Dielsalder Reaction and Other Pericyclic Reactions

Reactions Involving Free Radicals

Polymers

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Which of the following would produce a mixture of two isomers as the major products when allowed to react with Cl₂ and AlCl₃?

An amine substituent will coordinate to a Lewis acid such as AlCl₃,thereby deactivating the benzene ring.If the amine is converted to an amide,however,this coordination does not take place.Briefly explain why this is so,using a resonance structure to illustrate your answer.