Question
Considering the following reaction sequence, the correct statement(s) is(are)
JEE Advanced
Chemistry
Haloalkanes and Haloarenes
2022
JEE Advanced 2022 (Paper 2)
JEE Advanced Chemistry Question (2022) — Solution
Options
- A. Compounds P and Q are carboxylic acids.
- B. Compound S decolorizes bromine water.
- 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.
Answer
C. Compounds P and S react with hydroxylamine to give the corresponding oximes.
Step-by-step solution
Benzene undergoes friedel craft's reaction with succinic anhydride in presence of anhydrous AlCl 3 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. Compound S can not decolorizes bromine water. R 2 Cd 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.
Related: Chemistry — Haloalkanes and Haloarenes · All PYQ Banks