Grade 12Organic Chemistry

Among 1-chloropentane,2-chloropentane,and 1-Chloro-2,2-dimethylpropane which will give best sn1,sn2 and optical isomerism?

Jásmíné Síngh

5 Years agoGrade 12

Approved Tutor Answer5 Years ago

Let 1 chloropentane= a , 2 chloropentane = b, 1-chloro-2,2 dimethylpropane =c

Order of sn1: c>b>a (determined by stable carbocation after rearranging)

Order of sn2: a>b>c (determined by steric hindrance at the carbon being attacked and at its adjacent carbon)

Optical isomerism will only be shown by 2 chloropentane due to the presence of chiral carbon in it.

Carbon marked with red is chiral.

$CH_{3}-CH_{2}-CH_{2}-{\color{Red} C}H_{}(Cl)-CH_{3}$

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