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Solved: Starting with cyclohexane, how could the following
Chapter 13, Problem 36P(choose chapter or problem)
Starting with cyclohexane, how could the following compounds be prepared?
Questions & Answers
QUESTION:
Starting with cyclohexane, how could the following compounds be prepared?
ANSWER:
Solution 36P
(a)
Synthesis of cyclohexene form cyclohexane:
Cyclohexane reacts with bromine in the presence of light to form a bromocyclohexane.
Bromocyclohexane reacts with alcoholic KOH undergoes dehydrohalogenation to form cyclohexene.
The overall reaction is as follows:
(b)
Synthesis of 3-bromocyclohex-1-ene form cyclohexane:
Cyclohexane reacts with bromine in the presence of light to form a bromocyclohexane.
Bromocyclohexane reacts with alcoholic KOH undergoes dehydrohalogenation to form cyclohexene.
Cyclohexene reacts with NBS in presence of organic peroxide to get the desired product.
The overall reaction is as follows:
(c)
Synthesis of 3-methoxycyclohex-1-ene form cyclohexane:
Cyclohexane reacts with bromine in the presence of light to form a bromocyclohexane.
Bromocyclohexane reacts with alcoholic KOH undergoes dehydrohalogenation to form cyclohexene.
Cyclohexene reacts with NBS in presence of organic peroxide to get the desired product.
3-bromocyclohexene is then treated with sodium methoxide to generate 3-methoxycyclohexene according to Williamson ether synthesis.
The overall reaction is as follows:
(d)
Synthesis of 3-methylcyclohex-1-ene form cyclohexane:
Cyclohexane reacts with bromine in the presence of light to form a bromocyclohexane.
Bromocyclohexane reacts with alcoholic KOH undergoes dehydrohalogenation to form cyclohexene.
Cyclohexene reacts with NBS in presence of organic peroxide to get the desired product.
3-bromocyclohexene is then treated with lithium dimethyl cuprate to generate 3-methylcyclohexene according to Corey-House synthesis.
The overall reaction is as follows:
(e)
Synthesis of (1 R ,2 R )-2-methylcyclohexanol form cyclohexane:
Cyclohexane reacts with bromine in the presence of light to form a bromocyclohexane.
Bromocyclohexane reacts with alcoholic KOH undergoes dehydrohalogenation to form cyclohexene.
The derived cyclohexene is then treated with m-chloroperbenzoic acid in dichloromethane to get epoxide.
