IIT-JEE 2011 · Paper 2 · Chemistry Q17

ChemistryInteger+4Question 17 of 60

The maximum number of isomers (including stereoisomers) that are possible on mono-chlorination of the following compound, is

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Answer and worked solution

Official answer: 8

3-Methylpentane, $\ce{CH3CH2CH(CH3)CH2CH3}$ . Replace each kind of H:

Position	Product	Stereocentres	Isomers
C-1 ( $\ce{CH3}$ of ethyl)	1-chloro-3-methylpentane	C-3	2
C-2 ( $\ce{CH2}$ )	2-chloro-3-methylpentane	C-2, C-3	4
C-3 (CH)	3-chloro-3-methylpentane	none	1
3- $\ce{CH3}$	1-chloro-2-ethylbutane	none	1

Total $2+4+1+1=8$ .

Answer: 8

IIT-JEE 2011 · Paper 2, Chemistry question 17