Question

An organic compound $A\left(C_4{H}_{9}Cl\right)$ on reaction with $Na/diethyl$ ether gives a hydrocarbon which on monochlorination gives only one chloro derivative then, $A$ is:

• A. isobutyl chloride
• B. secondary butyl chloride
• C. tertiary butyl chloride
• D. n-butyl chloride

Answer 1

The correct option is C tertiary butyl chloride

An organic compound $A\left(C_4{H}_{9}Cl\right)$ on reaction with $Na/$ diethyl ether gives a hydrocarbon which on monochlorination gives only one chloro derivative then, $A$ is tertiary butyl chloride. The reaction of tertiary butyl chloride with $Na/$ diethyl ether to form 2,2,3,3-tetramethylbutane is an example of Wurtz coupling. The product 2,2,3,3-tetramethylbutane has only one type of H atom which is replaced with chlorine to give only one monochloro derivative.