JEE Main · 2004 · 24 Apr 2004 · Offline · General Organic Chemistry

Which of the following compound is not chiral?

(A)1-chloropentane✓ Correct
(B)3-chloro-2-methyl pentane
(C)1-chloro-2-methyl pentane
(D)2-chloropentane

Answer: (A)

Solution

A molecule is chiral only if it holds a carbon bonded to four different groups. In 1-chloropentane the chlorine sits on a terminal carbon that also carries two hydrogens, so that carbon has two identical substituents and cannot be a stereocentre, leaving the molecule achiral. Each of the other chloro-compounds does have a carbon with four different groups, so 1-chloropentane is the one that is not chiral.

JEE Main · 2004 · 24 Apr 2004 · Offline · Single correct option

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