Solution Found!
Using bromocyclohexane as a starting material, how could
Chapter 17, Problem 50P(choose chapter or problem)
Using bromocyclohexane as a starting material, how could you synthesize the following
compounds?
Questions & Answers
QUESTION:
Using bromocyclohexane as a starting material, how could you synthesize the following
compounds?
ANSWER:
Solution 50P
(a)
Treatment of bromocyclohexane with water molecule gives cyclohexanol.
Chromic acid is used as an oxidizing agent for the conversion of secondary alcohols to ketone. So, treatment of cyclohexanol with chromic acid gives cyclohexanone.
Treatment of cyclohexanone with methylmagnesium bromide (Grignard reagent) followed by the hydrolysis gives 1-methylcyclohexanol.
Dehydration of 1-methylcyclohexanol gives 1-methylcyclohex-1-ene (the desired product). Thus, the reaction is as follows:
(b)
Treatment of bromocyclohexane with magnesium in the presence of ether gives cyclohexylmagnesium bromine (a Grignard reagent).
Treatment of cyclohexylmagnesium bromide with formaldehyde followed by the hydrolysis gives cyclohexylmethanol (the desired product).
(c)
Treatment of bromocyclohexane with magnesium in the presence of ether gives cyclohexylmagnesium bromine (a Grignard reagent).
Treatment of cyclohexylmagnesium bromide with formaldehyde followed by the hydrolysis gives cyclohexylmethanol.
