Ncert Exercises & Solutions

Allyl chloride is hydrolysed more readily than n-propyl chloride. Why?

As It is very obivious that S

_{N}

1 mechanism will depend on the carbocation stability. Ally! chloride on hydrolysis gives resonance stabilised carbocation while there is no possibility of resonance is observad in the carbocationthat is formed by n-propyl chloride.

$C H_{2} = C H — C H_{2} C l \overset{- C l^{2}}{\to} C H_{2} = C H — \overset{+}{C} H_{2} + \bar{C} l$
$A l l y l c h l o r i d e$
$C H_{2} = C H — \overset{+}{C} H_{2} \leftrightarrow \overset{+}{C} H_{2} — C H = C H_{2}$
$C H_{2} — C H_{2} — C l \overset{- C l^{-}}{\to} C H_{3} — C H_{2} — \overset{+}{C} H_{2} + \bar{C} l$
$n - p r o p y l (N o t s t a b i l i s e d b y r e s o n a n c e)$
$c h l o r i d e$

Hence, allyl chloride will give hydrolysis much faster than n-propyl chloride.

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