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Which of the following compounds is not chiral?

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1-chloropentane

2-chloropentane

1-chloro-2-methyl pentane

3-chloro-2-methyl pentane

answer is A.

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Detailed Solution

Chiral carbon has all the four different groups attached to it.

(a) $C H_{3} C H_{2} C H_{2} C H_{2} C l$ no chiral carbon atom

(b) $C H_{3} \underset{Cl}{\underset{|}{C}} H C H_{2} C H_{2} C H_{3}$ one chiral carbon atom

(c) $C H_{3} C H_{2} C H_{2} \underset{\begin{matrix} | \\ C H_{3} \end{matrix}}{C} H C H_{2} C l$ one chiral carbon atom

(d) $C H_{3} \underset{\begin{matrix} | \\ C H_{3} \end{matrix}}{C} H - \underset{\begin{matrix} | \\ C l \end{matrix}}{C} H C H_{2} C H_{3}$ two chiral carbon atom

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