Organic Compounds Containing Halogens Question 176

Question: An organic compound $ A(C_4H_6Cl) $ on reaction with Na/diethyl ether gives a hydrocarbon, which on monochlorination gives only one chloro derivative. A is

[Kerala PMT 2004]

Options:

A) t-butyl chloride

B) s-butyl chloride

C) Isobutyl chloride

D) n-butyl chloride

E) None of these

Show Answer

Answer:

Correct Answer: A

Solution:

$ 2CH_3-\underset{Cl\ \ \ \ \ \ }{\overset{CH_3\ \ \ \ }{\mathop{\underset{|}{\overset{|}{\mathop{C}}}-CH_3}}}\underset{2Na}{\mathop{\xrightarrow{ether}}}CH_3-\underset{CH_3}{\overset{CH_3}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}–}}}\underset{CH_3\ \ \ \ \ }{\overset{CH_3\ \ \ \ }{\mathop{\underset{|}{\overset{|}{\mathop{C}}}-CH_3}}}+2NaCl $