Question 1

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 2

List the following compounds in order of decreasing reactivity toward electrophilic aromatic substitution: toluene, benzene, fluorobenzene, nitrobenzene, phenol.

Accepted Answer

phenol > toluene > b

Question 3

Give three different correct names for the structure.

Accepted Answer

2-amino-4-methylphen

Question 4

What is the best method for the preparation of p-chlorotoluene in high yield?

Accepted Answer

A) start with benzene; methylate; chlorinate 
B) start with benzene; chlorinate; methylate 
C) start with toluene; chlorinate 
D) start with chlorobenzene; methylate 
E) start with p-aminotoluene; NaNO2/HCl, 0°C; CuCl 
A) start with benzene; methylate; chlorinate 
B) start with benzene; chlorinate; methylate 
C) start with toluene; chlorinate 
D) start with chlorobenzene; methylate 
E) start with p-aminotoluene; NaNO2/HCl, 0°C; CuCl

Question 5

Which of the following aromatic rings is alkylated most rapidly by CH3CH2Cl/AlCl3?

Accepted Answer

A) benzene 
B) ethylbenzene 
C) chlorobenzene 
D) benzenesulfonic acid 
E) nitrobenzene 
A) benzene 
B) ethylbenzene 
C) chlorobenzene 
D) benzenesulfonic acid 
E) nitrobenzene

Question 6

Identify the reaction(s)below that give benzoic acid as a product.

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 7

Draw benzyl bromide.

Accepted Answer

The answer of Draw benzyl bromide....

Question 8

Predict the major organic 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 9

Which of the following is one of the resonance contributors of the intermediate produced in a Friedel-Crafts alkylation of benzene?

Accepted Answer

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

Question 10

What is the name of the following compound?

Accepted Answer

A) o-nitro-m-bromotoluene 
B) 3-bromo-6-nitrotoluene 
C) m-bromo-o-nitrotoluene 
D) 5-bromo-2-nitrotoluene 
E) 2-nitro-5-bromotoluene 
A) o-nitro-m-bromotoluene 
B) 3-bromo-6-nitrotoluene 
C) m-bromo-o-nitrotoluene 
D) 5-bromo-2-nitrotoluene 
E) 2-nitro-5-bromotoluene

Question 11

Name the following compound.

Accepted Answer

A) sec-hexylbenzene 
B) 3-phenylhexane 
C) 2-phenylhexane 
D) tert-hexylbenzene 
E) isohexylbenzene 
A) sec-hexylbenzene 
B) 3-phenylhexane 
C) 2-phenylhexane 
D) tert-hexylbenzene 
E) isohexylbenzene

Question 12

Why does benzene undergo electrophilic substitution rather than electrophilic addition?

Accepted Answer

When benzene undergoes electrophilic sub

Question 13

Provide the structure of benzoic acid.

Accepted Answer

The answer of Provide the structure of benzoic acid....

Question 14

Give the best product for the following reaction.

Accepted Answer

The answer of Give the best product for the following...

Question 15

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 16

Provide the major organic product of the following.

Accepted Answer

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

Question 17

Give the organic products from the following reaction.

Accepted Answer

The answer of Give the organic products from the following...

Question 18

Which of the following is not a correct statement about the electrophilic substitution mechanism of benzene?

Accepted Answer

A) Benzene functions as a nucleophile. 
B) Formation of a carbocation intermediate is the rate-determining step. 
C) The carbocation intermediate contains an sp3 hybridized carbon in the ring. 
D) The addition product is a frequent minor product. 
E) Aromaticity is regained by loss of H+. 
A) Benzene functions as a nucleophile. 
B) Formation of a carbocation intermediate is the rate-determining step. 
C) The carbocation intermediate contains an sp3 hybridized carbon in the ring. 
D) The addition product is a frequent minor product. 
E) Aromaticity is regained by loss of H+.

Question 19

What sequence of reagents can be used to accomplish the conversion shown below?

Accepted Answer

1. HNO₃, H₂SO₄ 2. Br₂, F

Question 20

What is the structure of p-toluidine?

Accepted Answer

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

Exam 19: Reactions of Benzene and Substituted Benzenes

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

List the following compounds in order of decreasing reactivity toward electrophilic aromatic substitution: toluene, benzene, fluorobenzene, nitrobenzene, phenol.

Give three different correct names for the structure.

What is the best method for the preparation of p-chlorotoluene in high yield?

Which of the following aromatic rings is alkylated most rapidly by CH3CH2Cl/AlCl3?

Identify the reaction(s)below that give benzoic acid as a product.

Draw benzyl bromide.

Predict the major organic product of the following reaction.

Which of the following is one of the resonance contributors of the intermediate produced in a Friedel-Crafts alkylation of benzene?

What is the name of the following compound?

Name the following compound.

Why does benzene undergo electrophilic substitution rather than electrophilic addition?

Provide the structure of benzoic acid.

Give the best product for the following reaction.

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

Provide the major organic product of the following.

Give the organic products from the following reaction.

Which of the following is not a correct statement about the electrophilic substitution mechanism of benzene?

What sequence of reagents can be used to accomplish the conversion shown below?

What is the structure of p-toluidine?

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds

Isomers: the Arrangement of Atoms in Space

Alkenes Thermodynamics and Kinetics

Reactions of Alkenes

Reactions of Alkynes Introduction to Multistep Synthesis

Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Substitution Reactions of Alkyl Halides

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

Reactions of Alkanes, 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 Alpha Carbon of Carbonyl Compounds

More About Amines Heterocylic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Catalysis

The Organic Mechanisms of the Coenzymes

The Chemistry of Metabolism

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

Which of the following aromatic rings is alkylated most rapidly by CH₃CH₂Cl/AlCl₃?