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JEE Advanced 2022 Paper 1 · Chemistry · General Organic Chemistry and Isomerism · hard

The total number of stereoisomers (counting each enantiomer separately, and counting constitutional isomers as different compounds) of all aldehydes…

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The total number of stereoisomers (counting each enantiomer separately, and counting constitutional isomers as different compounds) of all aldehydes and ketones having the molecular formula C6H12O\mathrm{C_6H_{12}O} (acyclic, containing one C=O\mathrm{C{=}O} group and no other functional group) is
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Answer: 18

Aldehydes are R−CHO\mathrm{R{-}CHO} with R=C5H11\mathrm{R}=\mathrm{C_5H_{11}}. There are 88 pentyl groups: n-pentyl, 2-pentyl, 3-pentyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl and neopentyl. Of the corresponding aldehydes, three have a stereocentre: 2-methylpentanal, 3-methylpentanal and 2,3-dimethylbutanal. So aldehydes give 8+3=118+3=11 stereoisomers. Ketones R−CO−R′\mathrm{R{-}CO{-}R'} with R+R′\mathrm{R}+\mathrm{R'} together C5\mathrm{C_5}: methyl with the four butyl groups (4 ketones) and ethyl with propyl or isopropyl (2 ketones), a total of 66. Only 3-methylpentan-2-one is chiral, so ketones give 6+1=76+1=7. Total =11+7=18=11+7=18. Answer: 18.
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