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

Considering the following reaction sequence,

the correct option(s) is(are)

  1. P=H2Pd, ethanol R=NaNO2HCl U=1.H3PO2
    2.KMnO4-KOH, heat
  2. P=SnHCl R = HNO2  
  3. U=1·CH3CH2OH
    2. KMnO4-KOH, heat
  4. R=H2Pd, ethanol

Solution

First step of the reaction involves reduction of nitro group to primary amine this can be done using Sn in presence of HCl or H2/Pd, but aromatic nitro compounds on reaction with LiAlH4produces azo products. 

Second step of the reaction involves diazotization, which involves the use of HNO2 (or) NaNO2 in HCl as the reagent ,Para toluene diazonium chloride formed is formed which on hydrolysis produces para-cresol.

And Para toluene diazonium chloride can be converted to benzoic acid by using H3PO2 or C2H5OH followed by reaction with KMnO4 in alkaline medium

P may be H2Pd, ethanol; SnHCl

R may be NaNO2/HCl;HNO2

U may be (i) H3PO2, (ii) KMnO4-KOH,Δ or (i) CH3-CH2-OH, (ii) KMnO4-KOH,Δ

Asked in: JEE Advanced 2022 (Paper 1)

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