The correct statement(s) about the compound $\mathrm{H}_3\mathrm{C}(\mathrm{HO})\mathrm{HC}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}(\mathrm{OH})\mathrm{CH}_3$ ($\mathbf{X}$) is(are)

(A) The total number of stereoisomers possible for $\mathbf{X}$ is 6; (D) If the stereochemistry about the double bond in $\mathbf{X}$ is cis, the number of enantiomers possible for $\mathbf{X}$ is 2

(B) The total number of diastereomers possible for $\mathbf{X}$ is 3

(C) If the stereochemistry about the double bond in $\mathbf{X}$ is trans, the number of enantiomers possible for $\mathbf{X}$ is 4

General Organic Chemistry — JEE Advanced · 2009 · 12 Apr 2009 · Paper 1 Question with Solution

The correct statement(s) about the compound

H_{3} C (HO) HC - CH = CH - CH (OH) CH_{3}

(

X

) is(are)

(A)The total number of stereoisomers possible for $X$ is 6✓ Correct
(B)The total number of diastereomers possible for $X$ is 3
(C)If the stereochemistry about the double bond in $X$ is trans, the number of enantiomers possible for $X$ is 4
(D)If the stereochemistry about the double bond in $X$ is cis, the number of enantiomers possible for $X$ is 2✓ Correct

Answer: (A), (D)

Solution

The compound has:

Two chiral centers (the two carbons bearing OH groups)
One double bond that can show cis-trans isomerism

With 2 chiral centers, the maximum number of stereoisomers = 2² = 4
With cis-trans isomerism: 4 × 2 = 8 possible stereoisomers

However, some may be identical due to symmetry.

(A) True: Total stereoisomers = 6 (accounting for symmetry considerations)

(B) False: The number of diastereomers is not 3

(C) False: For trans configuration, the number of enantiomers is not 4

(D) True: For cis configuration, there are 2 pairs of enantiomers, giving 2 enantiomers for each diastereomeric form

Therefore, the correct answers are (A) and (D).

JEE Advanced · 2009 · 12 Apr 2009 · Paper 1 · One or more correct options

JEE Advanced · 2009 · 12 Apr 2009 · Paper 1 · General Organic Chemistry

Solution

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