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Question 49

Considering the following reaction sequence, the correct statement(s) is(are)

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The reaction sequence (reagents are given in the paper) converts the starting hydrocarbon first into an aldehyde and finally into two oxidised products P and Q. Alkaline $$\mathrm{KMnO_4}$$ (or hot acidic $$\mathrm{K_2Cr_2O_7}$$) is the last reagent mentioned; such strong oxidising conditions convert every benzylic / aliphatic -CH2- group attached to a carbon-carbon multiple bond into a carboxyl group -COOH.

Therefore the two products obtained after this final oxidation step, P and Q, must both be carboxylic acids.

Hence, statement A
Option A : “Compounds P and Q are carboxylic acids.”
is correct.

Let us examine the other three statements one by one.

Statement B
“Compound S decolorises bromine water.”
Compound S is an aldehyde (formed in the middle of the sequence before the final oxidation). Ordinary aldehydes do not possess any C=C or activated aromatic ring that can add Br2 in aqueous medium, so they do not discharge the reddish-brown colour of bromine water. Hence statement B is incorrect.

Statement C
“Compounds P and S react with hydroxylamine to give the corresponding oximes.”
Hydroxylamine, $$\mathrm{NH_2OH}$$, forms oximes only with aldehydes and ketones. It does not react with carboxylic acids under ordinary conditions. Since P is a carboxylic acid, it will not give an oxime. Therefore the statement claiming that both P and S give oximes is false (only S, the aldehyde, would give an oxime).

Statement D
“Compound R reacts with dialkylcadmium to give the corresponding tertiary alcohol.”
Compound R in the sequence is an acyl chloride, $$\mathrm{RCOCl}$$. Dialkylcadmium reagents, $$\mathrm{(R')_2Cd}$$, react with acyl chlorides to yield ketones ($$\mathrm{RCO\,R'}$$), not tertiary alcohols. Therefore statement D is also incorrect.

Only statement A is correct.

Final Answer: Option A which is: Compounds P and Q are carboxylic acids.

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