Alkaline hydrolysis of which among the following compounds leads to the formation of a racemate ?

Options

A. 1-bromo-1-phenylethane
B. 1-chloro-3-methylbutane
C. Bromoethane
D. 1-chloropropane

Answer

A

Explanation

(a) `RX-KOH overset("Alkaline")underset("hydrolysis")rarr ROH +KX`
`underset("1-bromo-1-phenylethane")(CH_(3)-underset(C_(6)H_(5))underset("| ")"CH"-Br+KOH)rarrunderset("1-phenylethanol")(CH_(3)-overset(OH)overset("| ")underset(C_(6)H_(5))underset("| ")(C^(**))-H+KBr)`
Due to the formation of compound having chiral carbon, this hydrolysis will lead to the formation of a racemate.
(c) `underset("1-chloro-3-methylbutane")(CH_(3)-underset(CH_(3))underset("| ")"CH"-CH_(2)-CH_(2)Cl+KOHoverset(H_(3)O^(+))rarr underset("3-methylbutanol")(CH_(3)-underset(CH_(3))underset("| ")"CH"-CH_(2)-CH_(2)OH+KCl`
(c) `underset("Bromoethane")(CH_(3)CH_(2)Br)+KOH overset(H_(3)O^(+))rarr underset("Ethanol")(CH_(3)CH_(2)OH)+KBr`
(d) `underset("1. chloropropane")(CH_(3)CH_(2)CH_(2)Cl)+KOH overset(H_(3)O^(+))rarr undrset("propanol")(CH_(3)CH_(3)CH_(2)OH)+KCl`
Since, products in (b), (c) and (d) do not have any chiral carbon atom, so these cannot form a racemate.