Concept explainers
Interpretation:
The structural formulas involved in the sequence of given reactions for the formation of adipic acid or hexamethylene diamine are to be written, with given molecular formula of each compound and IR data of some compound.
Concept introduction:
A
Nylon is a polymer that consists of adipic acid and hexamethylene diamine as monomer units.
Nylon
The formation of Nylon
The addition of hydrogen to double or triple bond is a hydrogenation reaction.
Hydrogenation of
Infrared spectroscopy is a simple, instrumental technique, which helps to determine the presence of various functional groups.
It depends on the interactions of atoms or molecules with the electromagnetic radiation.
The molecules that have dipole moment are IR active and the molecules that do not have dipole moment are IR inactive.
Cyclohexanol shows IR peak at
Cyclic ketone shows IR peak at
Answer to Problem 1PP
Solution:
(a) The structures involved in the sequence are as follows:
(b) The structures involved in the sequence are as follows:
(c) The structures involved in the sequence are as follows:
(d) The structures involved in the sequence are as follows:
Explanation of Solution
a)
For the formation of adipic acid, first, benzene undergoes hydrogenation reaction to form cyclohexane, which then undergoes oxidation in the presence of catalyst to give cyclohexanol ( I.R. peak at
Hence, adipic acid is formed in this sequence of reactions.
b)
Here, adipic acid reacts with two molecules of ammonia to form ammonium salt of adipic acid. Then, on heating, this salt loses two molecules of water to form
The whole sequence can be written as
Hence, hexamethylene diamine is formed in this sequence of reactions.
c)
Here,
The whole sequence can be written as
Hence, hexamethylene diamine is formed in this sequence of reactions.
d)
Here, tetrahydrofuran undergoes chlorination in the presence of hydrochloric acid resulting in the formation of
The whole sequence can be written as
Hence, hexamethylene diamine is formed in this sequence of reactions.
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Chapter E Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
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