Question

1-chloro-3-methyl-2-pentene undergoes hydrolysis in warm water to give a mixture of 3-methyl-2-penten-1-ol and 3-methyl-1-penten-3-ol. Draw the structure of the intermediate's resonance contributor leading to the formation of 3-methyl-2-penten-1-ol.

Answer 1

See the figure

Step-by-step explanation:

As the first step, the Cl leaves the molecule and the double bond is moved to obtain a tertiary carbocation (the most stable one). Then the molecule of water attacks the primary carbon of the double bond, therefore the double bond moves again to the initial place. Finally, a hydronium ion is produced to remove the positive charge of the oxygen.