The number of stereoisomers possible for a compound of the molecular formula $\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}(\mathrm{OH})-\mathrm{Me}$ is :

JEE Main · 2009 · 12 Apr 2009 · Offline · General Organic Chemistry

The number of stereoisomers possible for a compound of the molecular formula

CH_{3} - CH = CH - CH (OH) - Me

is :

(A)3
(B)2
(C)4✓ Correct
(D)6

Answer: (C)

Solution

This molecule has two independent sources of stereoisomerism. The carbon-carbon double bond can take either the E or the Z arrangement, giving two possibilities, and the carbon bearing the hydroxyl group is a stereocentre that can be R or S, giving two more. Since the two features are independent, the total number of stereoisomers is

2 \times 2 = 4

JEE Main · 2009 · 12 Apr 2009 · Offline · Single correct option

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