Q13 / 54 · JEE Advanced 2022 (Paper 2) · Chemistry

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

Figure

  • Correct answer
    A
    Compounds P and Q are carboxylic acids.
  • B
    Compound S decolorizes bromine water.
  • Correct answer
    C
    Compounds P and S react with hydroxylamine to give the corresponding oximes.
  • D
    Compound R reacts with dialkylcadmium to give the corresponding tertiary alcohol.

Solution

Benzene undergoes friedel craft's reaction with succinic anhydride in presence of anhydrous AlCl3 to form P.The mechanism of the reaction is electrophilic substitution.

The keto group in P gets reduced on reaction Zn/Hg in HCl to form Q that is 4-phenylbutanoic acid.

This reacts with thionyl chloride to form R, that is 

4-Phenylbutanoyl chloride.

R again undergoes friedel craft's reaction to form S.

S gets reduced on reaction Zn/Hg in HCl to form a hydrocarbon as given in the reactions below.

Figure

Compound S can not decolorizes bromine water.

Figure

R2Cd is a less reactive nucleophile so reaction stops at carbonyl group.

Due to the presence of carbonyl group both P and S forms oxime with hydroxyl amine.

Hence, the correct answer is options: 'A', 'C'.

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