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JEE Advanced levelNumerical answerDifficulty 3 of 3ap033

Consider all the isomeric alcohols of molecular formula $C X_{5} H X_{12} O$ that are oxidised by $PCC$ in $CH X_{2} Cl X_{2}$ to ketones. Count enantiomers separately (each member of an enantiomeric pair counts as one compound) and do not count ethers. How many such compounds are there? Give the integer.

Numerical answer type, tolerance 0.5.

Answer: 5

Ketones come from secondary alcohols. The secondary

C X_{5} H X_{12} O

alcohols are pentan-2-ol (chiral, 2 enantiomers), pentan-3-ol (achiral, 1) and 3-methylbutan-2-ol (chiral, 2). Total = 2 + 1 + 2 = 5.

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