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Question
a solution of KOH hydrolyses CH3CHClCH2CH3 and CH3CH2CH2CH2Cl which one of these is easily hydrolysed and why?
a solution of KOH hydrolyses CH3CHClCH2CH3 and CH3CH2CH2CH2Cl which one of these is easily hydrolysed and why?
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Solution
The alkaline hydrolysis of primary haloalkane prefers SN1 mechanism and a secondary haloalkane also has a dominant SN1 mechanism in which no intermediate is formed and an alcohol is produced by highly unstable transition state.
So, here we have to search for most stable carbocation formed by the two compounds which will have more stable products.
Here,
a) CH3CHCl−CH2CH3 will produce a secondary carbocation while,
b) CH3CH2CH2CH2Cl will produce a primary carbocation.
Since the secondary carbocation is more stable so, easily hydrolysis will occur in CH3CH−Cl−CH2CH3
The alkaline hydrolysis of primary haloalkane prefers SN1 mechanism and a secondary haloalkane also has a dominant SN1 mechanism in which no intermediate is formed and an alcohol is produced by highly unstable transition state.
So, here we have to search for most stable carbocation formed by the two compounds which will have more stable products.
Here,
a) CH3CHCl−CH2CH3 will produce a secondary carbocation while,
b) CH3CH2CH2CH2Cl will produce a primary carbocation.
Since the secondary carbocation is more stable so, easily hydrolysis will occur in CH3CH−Cl−CH2CH3
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