Organic Compounds Containing Halogens Question 114

Question: An isomer of $ C_3H_6Cl_2 $ on boiling with aqueous KOH gives acetone. Hence, the isomer is

[UPSEAT 2000]

Options:

A) 2, 2-dichloropropane

B) 1, 2-dichloropropane

C) 1, 1-dichloropropane

D) 1, 3-dichloropropane

Show Answer

Answer:

Correct Answer: A

Solution:

$ \underset{\begin{smallmatrix} 2,2\text{ dichloropropane} \\ \text{(isomer of }C_3{H_6}C{l_2}\text{)} \end{smallmatrix}}{\mathop{CH_3-\underset{Cl}{\overset{Cl}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}-}}}CH_3}}+\underset{aqueous}{\mathop{2KOH}}\underset{-2KCl}{\mathop{\xrightarrow{boil}}}\underset{Unstable}{\mathop{CH_3-\underset{OH}{\overset{OH}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}-}}}CH_3}} $

$ \underset{\Delta }{\mathop{\xrightarrow{-H_2O}}}\underset{\text{(Acetone)}}{\mathop{CH_3-\overset{O}{\mathop{\overset{||}{\mathop{C}}}}-CH_3}} $