Question

Why is ch2=ch-ch2-cl more easily hydrolysed than ch3-ch2-ch2-cl?

Answer 1

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Answer 2

Hey Dear,

● Explanation -

• Reactivity towards hydrolysis depends on formation of carbocation intermediate.
• CH3=CH-CH2-Cl on removal of chloride ion forms allyl carbocation.
• Allyl carbocation shows resonace effect and thus is highly stable carbocation.
• CH3-CH2-CH2-Cl on removal of chloride ion forms ethyl carbocation.
• Propyl carbocation stabilizes to some extent by inductive effect but not as much as allyl carbocation.
• Therefore, CH3=CH-CH2-Cl undergo hydrolysis more easily than CH3-CH2-CH2-Cl.

Hope this helps you. Thanks for asking..