(a)
Interpretation:
The compounds mesitylene, toluene, and
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an 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 16.44AP
The compounds mesitylene, toluene, and
Explanation of Solution
The structure of mesitylene, toluene, and
Figure 1
The reaction of any
The methyl group is electron-donating group. It activates the phenyl ring. The toluene has only one methyl group attached to it. Therefore, it will be least reactive towards
The order of reactivity toward nitration reaction is shown below.
The increasing order of reactivity towards toward
(b)
Interpretation:
The compounds chlorobenzene, benzene, and nitrobenzene are to be arranged in increasing order of increasing reactivity toward
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an 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 16.44AP
The compounds chlorobenzene, benzene, and nitrobenzene are arranged in increasing order of increasing reactivity toward
Explanation of Solution
The structure of chlorobenzene, benzene, and nitrobenzene are shown below.
Figure 2
The reaction of any aromatic compound with
The nitro and chloro groups are electron-withdrawing groups. Therefore, the reactivity of the chlorobenzene and nitrobenzene will be less than that of benzene. The nitro group is stronger deactivating group than chloro group. Therefore, the order of reactivity toward nitration reaction is shown below.
The increasing order of reactivity towards toward
(c)
Interpretation:
The compounds
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an 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 16.44AP
The compounds
Explanation of Solution
The structure of
Figure 3
The reaction of any aromatic compound with
The methoxy group and chloro groups are ortho and para directing groups. The methoxy group is electron releasing group and chloro group is electron-withdrawing group.
Therefore, the reactivity of anisole will be highest among the rest of the compound toward
The order of reactivity toward nitration reaction is shown below.
The increasing order of reactivity towards toward
(d)
Interpretation:
The compounds acetophenone,
Concept introduction:
The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an 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 16.44AP
The compounds acetophenone,
Explanation of Solution
The structure of acetophenone,
Figure 4
The reaction of any aromatic compound with
The acetyl group and bromo group is electron-withdrawing groups and methoxy group is electron releasing group. Acetophenone has a ring activating group attached on it. Therefore, it is most reactive toward nitration reaction among the rest of the compound. The compound
The increasing order of reactivity towards toward
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Chapter 16 Solutions
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