Question

Of the two alcohols; (a) CH₂=CH—CH₂OH and (b) CH₂=CH—CH₂—CH₂OH, which one will react more easily with conc. HCl in the presence of ZnCl₂?

Answer 1

CH₂ = CH–CH₂OH will be more reactive than CH₂ = CH–CH₂CH₂OH

Reason: In the reaction of alcohol with the HCl in presence of ZnCl₂, cleavage of the C–O bond takes place. In first alcohol, OH group is present to the allylic carbon so formation of partial double bond between C–2 and C–3 takes place due to resonance resulting weakening of bond between C and O.

Answer 2

CH₂ = CH-CH₂OH

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