
(a)
Interpretation:
The laboratory synthesis of
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic

Answer to Problem 16.43AP
The laboratory synthesis of
Explanation of Solution
The structure of
Figure 1
The methyl is an ortho and para directing group and nitro is a meta directing group. the compound is para compound. Therefore, the benzene will first undergo methylation reaction with chloromethane and
Figure 2
The toluene will undergo nitration reaction with nitric acid in sulfuric acid to from ortho and para-substituted compounds. The para-substituted gets separated from ortho compound with the help of fractional distillation process. The corresponding chemical reaction is shown below.
Figure 3
The laboratory synthesis of
(b)
Interpretation:
The laboratory synthesis of
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction. The rate of electrophilic aromatic substitution reaction depends on the substituted group on the aromatic ring. The ring deactivating group retards the electrophilic aromatic substitution reaction and ring activating group enhances the electrophilic aromatic substitution reaction.

Answer to Problem 16.43AP
The laboratory synthesis of
Explanation of Solution
The structure of
Figure 4
Benzene reacts with an excess of bromine gas in the presence of a
Figure 5
The laboratory synthesis of
(c)
Interpretation:
The laboratory synthesis of
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction. The rate of electrophilic aromatic substitution reaction depends on the substituted group on the aromatic ring. The ring deactivating group retards the electrophilic aromatic substitution reaction and ring activating group enhances the electrophilic aromatic substitution reaction.

Answer to Problem 16.43AP
The laboratory synthesis of
Explanation of Solution
The structure of
Figure 6
Benzene reacts with chlorine gas in the presence of a catalyst
Figure 7
The chlorobenzene undergoes Friedel Craft acylation reaction with acetyl chloride in the presence of
Figure 8
The laboratory synthesis of
(d)
Interpretation:
The laboratory synthesis of
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction. The rate of electrophilic aromatic substitution reaction depends on the substituted group on the aromatic ring. The ring deactivating group retards the electrophilic aromatic substitution reaction and ring activating group enhances the electrophilic aromatic substitution reaction.

Answer to Problem 16.43AP
The laboratory synthesis of
Explanation of Solution
The structure of
Figure 9
The benzene molecule will undergo sulfonation reaction with sulfuric acid. The electrophile
Figure 10
The benzenesulfonic acid will undergo nitration reaction with fuming nitric acid in sulfuric acid to form
Figure 11
The laboratory synthesis of
(e)
Interpretation:
The laboratory synthesis of
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction. The rate of electrophilic aromatic substitution reaction depends on the substituted group on the aromatic ring. The ring deactivating group retards the electrophilic aromatic substitution reaction and ring activating group enhances the electrophilic aromatic substitution reaction.

Answer to Problem 16.43AP
The laboratory synthesis of
Explanation of Solution
The structure of
Figure 12
Benzene reacts with chlorine gas in the presence of a catalyst
Figure 13
The chlorobenzene will undergo nitration reaction with nitric acid in sulfuric acid to form
Figure 14
The laboratory synthesis of
(f)
Interpretation:
The laboratory synthesis of
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction. The rate of electrophilic aromatic substitution reaction depends on the substituted group on the aromatic ring. The ring deactivating group retards the electrophilic aromatic substitution reaction and ring activating group enhances the electrophilic aromatic substitution reaction.

Answer to Problem 16.43AP
The laboratory synthesis of
Explanation of Solution
The structure of
Figure 15
The benzene will undergo nitration reaction with nitric acid in sulfuric acid to form nitrobenzene. The nitro group is a ring deactivating group and meta directing group. Therefore, some strong condition is required to substitute another electrophile on it. The nitrobenzene reacts with fuming nitric acid and sulfuric acid to form
Figure 16
The laboratory synthesis of
(g)
Interpretation:
The laboratory synthesis of
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction. The rate of electrophilic aromatic substitution reaction depends on the substituted group on the aromatic ring. The ring deactivating group retards the electrophilic aromatic substitution reaction and ring activating group enhances the electrophilic aromatic substitution reaction.

Answer to Problem 16.43AP
The laboratory synthesis of
Explanation of Solution
The structure of
Figure 17
The benzene will first undergo methylation reaction with chloromethane and
Figure 18
The toluene will undergo nitration reaction with nitric acid in sulfuric acid to form ortho and para-substituted compounds. The para-substituted gets separated from ortho compound with the help of fractional distillation process. The corresponding chemical reaction is shown below.
Figure 19
The compound
Figure 20
The laboratory synthesis of
(h)
Interpretation:
The laboratory synthesis of
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction. The rate of electrophilic aromatic substitution reaction depends on the substituted group on the aromatic ring. The ring deactivating group retards the electrophilic aromatic substitution reaction and ring activating group enhances the electrophilic aromatic substitution reaction.

Answer to Problem 16.43AP
The laboratory synthesis of
Explanation of Solution
The structure of
Figure 21
The benzene will first undergo methylation reaction with chloromethane and
Figure 22
The toluene will undergo nitration reaction with nitric acid in sulfuric acid to form ortho and para-substituted compounds. The para-substituted gets separated from ortho compound with the help of fractional distillation process. The corresponding chemical reaction is shown below.
Figure 23
The compound
Figure 24
The laboratory synthesis of
(i)
Interpretation:
The laboratory synthesis of
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction. The rate of electrophilic aromatic substitution reaction depends on the substituted group on the aromatic ring. The ring deactivating group retards the electrophilic aromatic substitution reaction and ring activating group enhances the electrophilic aromatic substitution reaction.

Answer to Problem 16.43AP
The laboratory synthesis of
Explanation of Solution
The structure of
Figure 25
The benzene will first undergo ethylation reaction with chloromethane and
Figure 26
The ethylbenzene undergoes Friedel Craft acylation reaction with acetyl chloride in the presence of
Figure 27
The compound
Figure 28
The laboratory synthesis of
(j)
Interpretation:
The laboratory synthesis of cyclopentylbenzene from benzene and any other reagents is to be predicted.
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction. The rate of electrophilic aromatic substitution reaction depends on the substituted group on the aromatic ring. The ring deactivating group retards the electrophilic aromatic substitution reaction and ring activating group enhances the electrophilic aromatic substitution reaction.

Answer to Problem 16.43AP
The laboratory synthesis of cyclopentylbenzene from benzene and any other reagents is shown below.
Explanation of Solution
The structure of cyclopentylbenzene is shown below.
Figure 29
Benzene reacts with cyclopentene in the presence of sulfuric acid to form cyclopentyl benzene. The sulfuric acid acts as a catalyst to generate carbocation from cyclopentene. This carbonation acts as an electrophile and attacks the benzene ring. The corresponding chemical reaction is shown below.
Figure 30
The laboratory synthesis of cyclopentylbenzene from benzene and any other reagents is shown in Figure 30.
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Chapter 16 Solutions
Organic Chemistry
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