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Choose the Best Answer · Q17

Q.The most easily hydrolysed molecule under SN1 condition is a) allyl chloride b) ethyl chloride c) isopropyl chloride d) benzyl chloride

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Step 1. SN1 hydrolysis rate tracks how stable/easily-formed the intermediate carbocation is -- the more stabilised the cation, the faster the (rate-determining) ionisation step, and so the faster the overall SN1 hydrolysis.

Step 2. Ethyl chloride (primary) and isopropyl chloride (secondary) give only simple alkyl carbocations, stabilised solely by weak hyperconjugation/induction -- both react sluggishly by SN1 (a primary cation especially is very unstable).

Step 3. Allyl chloride's cation is resonance-stabilised by the adjacent C=C double bond (delocalised over two carbons) -- a real stabilisation, faster than the simple alkyl cases. …

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