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Meso Compounds

An optically ...

Question

An optically active alcohol A $(C_{6} H_{10} O)$ absorbs two moles of hydrogen per mole of A upon catalytic hydrogenation and gives a product B.The compound B is resistant to oxidation by $C r O_{3}$ and does not show any optical activity.Deduce the structures of A and B.

A

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B

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C

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D

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Solution

The correct option is A
(i) Since B is resistant to oxidation, it must be tert.alcohol.
(ii) Since B is optically inactive, it must have atleast two similar alkyl groups.
Thus the five carbon atoms can be adjusted into three alkyl groups(of which two are similar)either as
$- C H_{3}, - C H_{3}$ and $C_{3} H_{7}$ or as $C_{2} H_{5}, - C_{2} H_{5}$ and $- C H_{3}$ .Thus the possible structure of alcohol B is either

Hence the corresponding compound A is either

However compound A is optically active so its structure should be
which contains a chiral C-atom.
$∴$

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Similar questions

Q. An optically active alcohol A

(C_{6} H_{10} O)

absorbs 2 mol of hydrogen per mole of A upon catalytic hydrogenation and gives a product B. The compound B is resistant to oxidation by

C r O_{3}

and does not show any optical activity. Deduce the structures of A and B.

Q. An organic compound (A) containing C, H, and O (16.32%) does not decolourise bromine water and does not give any precipitate with ammoniacal

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per mole of (A) to give a solid derivative. The monobromo derivative of (A) shows optical activity. If (A) is optically inactive, suggest the number of hydrogen atoms present in the structure of compound (A).

Five isomeric alkenes (all positional isomers)

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E

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show geometrical isomerism.

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Alkene liberating least heat on hydrogenation is:

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Q. An organic compound A has molecular formula

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