Question 1

Which of the following compounds reacts most slowly during nitration?

Accepted Answer

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

Question 2

Propose a synthesis of the following compound benzene.

Accepted Answer

The answer of Propose a synthesis of the following compound...

Question 3

Provide the structure of the major organic product of the following reaction.

Accepted Answer

The answer of Provide the structure of the major organic...

Question 4

What is the major product of the following reaction?

Accepted Answer

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

Question 5

What is the major organic product of the reaction shown below?

Accepted Answer

The answer of What is the major organic product of...

Question 6

Identify the best product for the following reaction.

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 7

Draw the four major resonance structures of the intermediate which results when o-nitrochlorobenzene is treated with NaOH.

Accepted Answer

The answer of Draw the four major resonance structures of...

Question 8

Does cycloheptatriene have a higher or lower pKa than cyclopentadiene? Explain.

Accepted Answer

Cycloheptatriene is a weaker acid than c

Question 9

In nitration of benzene rings,what is the role of sulfuric acid?

Accepted Answer

A) It protonates the benzene ring in the first step. 
B) It protonates the -OH group of the nitric acid. 
C) It protonates the nitrogen atom of the nitric acid. 
D) It deprotonates the -OH group of the nitric acid. 
E) none of the above 
A) It protonates the benzene ring in the first step. 
B) It protonates the -OH group of the nitric acid. 
C) It protonates the nitrogen atom of the nitric acid. 
D) It deprotonates the -OH group of the nitric acid. 
E) none of the above

Question 10

Identify the best product for the following reaction.

Accepted Answer

A)    
B)    
C)    
D)    
E)    
A)    
B)    
C)    
D)    
E)

Question 11

Which of the following structures is the most important contributor to the resonance hybrid formed when anisole undergoes o-bromination?

Accepted Answer

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

Question 12

Draw benzyl bromide.

Accepted Answer

The answer of Draw benzyl bromide....

Question 13

What is the major product of the following reaction?

Accepted Answer

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

Question 14

In electrophilic aromatic substitution reactions,a chlorine substituent is

Accepted Answer

A) a deactivator and a m-director 
B) a deactivator and an o,p-director 
C) an activator and a m-director 
D) an activator and an o,p-director 
E) none of the above 
A) a deactivator and a m-director 
B) a deactivator and an o,p-director 
C) an activator and a m-director 
D) an activator and an o,p-director 
E) none of the above

Question 15

Identify the reaction(s)below that give benzoic acid as a product.You may choose more than one answer.

Accepted Answer

A) 1-phenylethanol + manganese dioxide + heat 
B) 1-phenylethanol + sodium dichromate + acid + heat 
C) tert-butylbenzene + sodium dichromate + acid + heat 
D) ethylbenzene + sodium dichromate + acid + heat 
E) phenylmethanol + manganese dioxide + heat 
A) 1-phenylethanol + manganese dioxide + heat 
B) 1-phenylethanol + sodium dichromate + acid + heat 
C) tert-butylbenzene + sodium dichromate + acid + heat 
D) ethylbenzene + sodium dichromate + acid + heat 
E) phenylmethanol + manganese dioxide + heat

Question 16

What is the best method for carrying out the following reaction?

Accepted Answer

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

Question 17

Provide a detailed,stepwise mechanism for the reaction of benzene with Br2 and FeBr3.Make sure to include the activating reaction between Br2 and FeBr3 in your mechanism.

Accepted Answer

Question 18

What is the best method for the preparation of m-dibromobenzene from benzene?

Accepted Answer

A) nitrate; Sn/HCl; NaNO2/HCl,0°C; brominate twice 
B) nitrate; Sn/HCl; NaNO2/HCl,0°C; brominate twice; H3PO2 
C) nitrate; Sn/HCl; NaNO2/HCl,0°C; H3PO2; brominate twice 
D) nitrate; brominate; Sn/HCl; NaNO2/HCl,0°C; CuBr 
E) brominate twice 
A) nitrate; Sn/HCl; NaNO2/HCl,0°C; brominate twice 
B) nitrate; Sn/HCl; NaNO2/HCl,0°C; brominate twice; H3PO2 
C) nitrate; Sn/HCl; NaNO2/HCl,0°C; H3PO2; brominate twice 
D) nitrate; brominate; Sn/HCl; NaNO2/HCl,0°C; CuBr 
E) brominate twice

Question 19

The name 2,4,6-tribromobenzene is incorrect.Which of the following is the correct name?

Accepted Answer

A) tribromobenzene 
B) m,m-dibromobromobenzene 
C) 3,5-dibromobromobenzene 
D) 1,3,5-tribromobenzene 
E) m,m,m-tribromobenzene 
A) tribromobenzene 
B) m,m-dibromobromobenzene 
C) 3,5-dibromobromobenzene 
D) 1,3,5-tribromobenzene 
E) m,m,m-tribromobenzene

Question 20

What purpose does FeCl3 serve in the electrophilic aromatic substitution reaction between chlorine and benzene?

Accepted Answer

A) It serves as a radical initiator to produce the chlorine radical needed to propagate the chain reaction. 
B) It functions by destabilizing the carbocationic intermediate and thereby increases the rate of H+ loss. 
C) It serves as a Lewis base catalyst by reacting with Cl2 to generate chloride ions. 
D) It functions by destabilizing the benzene through formation of a π-complex. 
E) It serves as a Lewis acid catalyst by reacting with the Cl2 and thereby activates it toward attack by benzene's π electrons. 
A) It serves as a radical initiator to produce the chlorine radical needed to propagate the chain reaction. 
B) It functions by destabilizing the carbocationic intermediate and thereby increases the rate of H+ loss. 
C) It serves as a Lewis base catalyst by reacting with Cl2 to generate chloride ions. 
D) It functions by destabilizing the benzene through formation of a π-complex. 
E) It serves as a Lewis acid catalyst by reacting with the Cl2 and thereby activates it toward attack by benzene's π electrons.

Exam 18: Reactions of Benzene and Substituted Benzenes

Which of the following compounds reacts most slowly during nitration?

Propose a synthesis of the following compound benzene.

Provide the structure of the major organic product of the following reaction.

What is the major product of the following reaction?

What is the major organic product of the reaction shown below?

Identify the best product for the following reaction.

Draw the four major resonance structures of the intermediate which results when o-nitrochlorobenzene is treated with NaOH.

Does cycloheptatriene have a higher or lower pKa than cyclopentadiene? Explain.

In nitration of benzene rings,what is the role of sulfuric acid?

Identify the best product for the following reaction.

Which of the following structures is the most important contributor to the resonance hybrid formed when anisole undergoes o-bromination?

Draw benzyl bromide.

What is the major product of the following reaction?

In electrophilic aromatic substitution reactions,a chlorine substituent is

Identify the reaction(s)below that give benzoic acid as a product.You may choose more than one answer.

What is the best method for carrying out the following reaction?

Provide a detailed,stepwise mechanism for the reaction of benzene with Br2 and FeBr3.Make sure to include the activating reaction between Br2 and FeBr3 in your mechanism.

What is the best method for the preparation of m-dibromobenzene from benzene?

The name 2,4,6-tribromobenzene is incorrect.Which of the following is the correct name?

What purpose does FeCl3 serve in the electrophilic aromatic substitution reaction between chlorine and benzene?

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds: Nomenclature, physical Properties, and Structure

Isomers: the Arrangement of Atoms in Space

Alkenes: Structure,nomenclature,and an Introduction to Reactivity - Thermodynamics and Kinetics

The Reactions of Alkenes - the Stereochemistry of Addition Reactions

The Reactions of Alkynes - Introduction to Multistep Synthesis

Delocalized Electrons: Their Effect on Stability, pka, and the Products of a Reaction - Aromaticity and Electronic Effects: an Introduction to the Reactions of Benzene

Substitution and Elimination Reactions of Alkyl Halides

Reactions of Alcohols, ethers, epoxides, amines and Sulfur-Containing Compounds

Organometallic Compounds

Radicals

Mass Spectrometry,infrared Spectroscopy,and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions at the Α-Carbon

More About Amines - Reactions of Heterocylic Compounds

The Organic Chemistry of Carbohydrates

Amino Acids,peptides,and Proteins

Catalysis in Organic Reactions and in Enzymatic Reactions

The Organic Chemistry of the Coenzymes, compounds Derived From Vitamins

The Organic Chemistry of the Metabolic Pathways

The Organic Chemistry of Lipids

The Chemistry of the Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Provide a detailed,stepwise mechanism for the reaction of benzene with Br₂ and FeBr₃.Make sure to include the activating reaction between Br₂ and FeBr₃ in your mechanism.

What purpose does FeCl₃ serve in the electrophilic aromatic substitution reaction between chlorine and benzene?