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JEE Advance - Chemistry (2011 - Paper 1 Offline - No. 17)

An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through the following sequence of reactions, in which Q is an intermediate organic compound.

An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through the following sequence of reactions, in which Q is an intermediate organic compound.

An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through the following sequence of reactions, in which Q is an intermediate organic compound.

The structure of the compound Q is
IIT-JEE 2011 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 24 English Option 1
IIT-JEE 2011 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 24 English Option 2
IIT-JEE 2011 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 24 English Option 3
IIT-JEE 2011 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 24 English Option 4

Explanation

(i) When 3,3-dimethyl but-1-yne reacts with dil. $\mathrm{H}_2 \mathrm{SO}_4$ in presence of $\mathrm{HgSO}_4$, ketone is formed.

IIT-JEE 2011 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 24 English Explanation 1

(ii) The ketone is reduced to secondary alcohol in presence of sodium borohydride $\left(\mathrm{NaBH}_4\right)$ ethanol).

IIT-JEE 2011 Paper 1 Offline Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 24 English Explanation 2

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