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Concept explainers
Interpretation:
The equations for the preparation of each of the given compounds from benzene or toluene and any necessary organic or inorganic reagents are to be written.
Concept Introduction:
In electrophilic
When aromatic ring having two comparably activated positions then the substitution usually takes place at the less hindered position.
The reagent zinc amalgam and concentrated hydrochloric acid is use to convert a carbonyl group into methylene unit. This reaction is known as Clemmenson’s reduction.
In Friedel-Crafts acylation, acyl halides are used to yield aryl
In Friedel-Crafts
A mixture of nitric acid and sulfuric acid produces a nitronium ion which behaves as an electrophile in electrophilic aromatic substitution reactions.
Reagent bromine in acetic acid indicates bromination reaction.
Reagent sulfur trioxide in sulfuric acid indicates sulfonation reaction.
Oxidation of benzylic carbon atom is done using the
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Answer to Problem 49P
Solution:
a) Reaction equations for the synthesis of isopropyl benzene from benzene is shown below:
b) Reaction equations for the synthesis of
c) Reaction equations for the synthesis of
d) Reaction equations for the synthesis of
e) Reaction equations for the synthesis of
f) Reaction equations for the synthesis of
g) Reaction equations for the synthesis of
h) Reaction equations for the synthesis of
i) Reaction equations for the synthesis of
j) Reaction equations for the synthesis of
k) Reaction equations for the synthesis of
l) Reaction equations for the synthesis of
m) Reaction equations for the synthesis of
n) Reaction equations for the synthesis of
Explanation of Solution
a) The structure for isopropyl benzene is:
Benzene undergoes Friedel-Crafts alkylation with isopropyl chloride with aluminum chloride to yield isopropyl benzene as shown below:
b) The structure of
In the above structure, the isopropyl substituents, isopropyl and sulfonic acid are para to each other.
Benzene undergoes Friedel-Crafts alkylation with isopropyl chloride with aluminum chloride to yield isopropyl benzene. In the second step, isopropyl benzene is treated with the solution of sulfur trioxide in sulfuric acid yields
Reaction equations for the synthesis of
c) The structure of
In the structure for the final product, the phenyl group and a bromine atom is attached to
d) The structure of
To get this product, toluene should be the starting compound that must be used. In the first step, toluene undergoes Friedel-Crafts alkylation with tertiary butyl chloride with aluminum chloride to yield tert-butyl toluene. In the second step, the tert-butyl toluene undergoes a nitration reaction to yield the product in which the nitro substituent is attached to the ortho position of the methyl group and meta position of the tertiary butyl group. Due to steric hindrance, the product in which the nitro group is attached at the ortho position of the tertiary butyl group is less favorable.
Reaction equations for the synthesis of
e) The structure for
To get this product, benzene should be the starting compound that must be used. In the first step, benzene undergoes Friedel-Crafts acylation with acyl chloride with aluminum chloride to yield
Reaction equations for the synthesis of
f) The structure of
In order to get this product, benzene should be the starting compound that must be used. In the first step, benzene undergoes chlorination reaction in presence of a Lewis acid such as aluminum chloride to yield chlorobenzene. In the second step, chlorobenzene undergoes Friedel-Crafts acylation with acyl chloride with aluminum chloride to yield
Reaction equations for the synthesis of
g) The structure for
On order to get this product, toluene should be the starting compound that must be used. In the first step, toluene undergoes Friedel-Crafts acylation with acyl chloride with aluminum chloride to yield
Reaction equations for the synthesis of
h) The structure for
To get this product, toluene should be the starting compound that must be used. In the first step, toluene undergoes Friedel-Crafts alkylation with ethyl chloride with aluminum chloride to yield
Reaction equations for the synthesis of
i) The structure for
To get this product, toluene should be the starting compound that must be used.
In the first step, toluene undergoes oxidation of benzylic carbon atom in toluene with
In the second step, benzoic acid undergoes a nitration reaction with a mixture of nitric acid and sulfuric acid giving
In the third step,
Reaction equations for the synthesis of
j) The structure for
To get the desired product, toluene should be the starting compound that must be used.
In the first step, toluene with nitric acid and sulfuric acid undergoes a nitration reaction giving
In the second step, benzoic acid undergoes bromination reaction in presence of a Lewis acid such as Iron (III) bromide to yield
In the third step,
Reaction equations for the synthesis of
k) The structure for
To get this product, benzene should be the starting compound that must be used.
In the first step, benzene undergoes Friedel-Crafts acylation with octanyl chloride with aluminum chloride.
In the second step, the carbonyl group is reduced in the presence of
Reaction equations for the synthesis of
l) The structure of
In order to get this product, benzene should be the starting compound that must be used.
In the first step, benzene undergoes Friedel-Crafts acylation with octenyl chloride with aluminum chloride.
In the second step, the carbonyl group is reduced to the hydroxyl group in the presence of
In the third step, the resulting alcohol is heated with sulfuric acid at high temperatures to yield
Reaction equations for the synthesis of
m) The structure of
To get this product, benzene should be the starting compound that must be used.
In the first step, benzene undergoes Friedel-Crafts acylation with octanyl chloride with aluminum chloride.
In the second step, the carbonyl group is reduced to the hydroxyl group in the presence of
In the third step, the resulting alcohol is heated with sulfuric acid at high temperatures to yield
In the fourth step,
Reaction equations for the synthesis of
n) The structure of
To get the required product, benzene should be the starting compound that must be used.
In the first step, benzene undergoes Friedel-Crafts acylation with tertiary butyl chloride with aluminum chloride giving tert-butyl toluene.
In the second step again, the tert-butyl toluene undergoes Friedel-Crafts acylation with tertiary butyl chloride with aluminum chloride giving
In the third step,
Reaction equations for the synthesis of
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Chapter 13 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
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