
Concept explainers
Interpretation:
The series of equations for the preparation of each of the given compound from the designated starting material using suitable organic or inorganic reagents is to be written.
Concept introduction:
The conjugate base of alkyne acts as a good nucleophile. On reaction with primary
In hydration of alkynes, a molecule of water gets added to a molecule of alkyne.Hydrogen atom gets attached to the less substituted triple bonded carbon atom, and hydroxyl groupgetsbonded to the more substituted triple bonded carbon atom and forms a
Geminal and vicinal dihalides, on reaction with a strong base, undergo double dehydrohalogenation and form alkynes.
On halogenation, alkynes form vicinal dihalides and, on reaction with hydrogen halides, they form geminal dihalides in two steps.
Primary alcohol can be converted to primary alkyl bromide by reaction with sodium bromide in acidic condition.

Answer to Problem 36P
Solution:
a)
b)
c)
d)
e)
f)
g)
h)
Explanation of Solution
a)
The
The synthesis of
b)
The
The synthesis of
c)
The
The synthesis of
d)
Acetylene on treatment with sodium amide, gives sodium salt of acetylene. The sodium salt of acetylene on treatment with ethyl bromide gives
The synthesis of
e)
Acetylene on treatment with sodium amide, gives sodium salt of acetylene. In presence of organoboron,
The synthesis of
f)
In presence of organoboron,
The synthesis of
g)
Cyclopentadecene on halogenation with
The synthesis of
h)
In presence of base sodium amide, the given alkyne gives sodium salt of alkyne. The sodium salt of alkyne on treatment with bromomethane adds one methyl group to alkyne, which on partial hydrogenation with Lindlar catalyst gives required cis alkene.
The synthetic route is as follows:
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Chapter 9 Solutions
Organic Chemistry - Standalone book
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
