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Distinguishing Test of Terminal and Non Terminal Alkynes

1,4 Pentadien...

Question

1,4 Pentadiene reacts with excess of $H C l$ in the presence of benzoyl peroxide to give compound $X$ , which upon reaction with excess of $M g$ in dry ether forms $Y$ . Compound $Y$ on treatment with ethyl acelate followed by treatment with dilute acid yields $Z$ . Identify the structure of compounds $X, Y$ and $Z$ .

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Solution

The structures of compounds X,Y and Z are as shown. The first step is the addition of HCl to C $=$ C double bond. The addition follows Markownikoff's rule. -Cl is added to more substituted C atom. The presence of benzoyl peroxide does not affects the regioselectivity as peroxide effect is observed only in case of HBr addition. This is followed by formation of grignard reagent and reaction with ethyl acetate followed by acid hydrolysis. The end product is a mixture of a tertiary alcohol and ethanol.

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