MolSynapsequestion bank
MolSynapse / Question bank / Structural Identification and Practical Organic Chemistry / Structure determination from reaction sequences
JEE Advanced levelOne or more correct optionsDifficulty 3 of 3si119

A compound X () gives an orange precipitate with 2,4-DNP and a yellow precipitate with , but does not reduce Tollens reagent. Vigorous oxidation of X with hot alkaline and acidification gives benzene-1,4-dicarboxylic acid. Select the correct statement(s).

  1. AThe IR spectrum of X shows a broad band near for an O-H group.
  2. BX is a para-disubstituted benzene derivative.
  3. CClemmensen reduction of X gives 1-ethyl-4-methylbenzene.
  4. DThe haloform reaction of X followed by acidification gives 4-methylbenzoic acid.

Answer: B, C, D

Oxidation to terephthalic acid shows two para side chains. The iodoform and DNP tests identify a methyl ketone, so X is (4-methylacetophenone, ). Clemmensen gives 1-ethyl-4-methylbenzene, and the haloform reaction converts into , giving 4-methylbenzoic acid. X has no O-H group, only a C=O stretch near .
Practice Structural Identification and Practical Organic Chemistry More on Structure determination from reaction sequences
Previous questionNext question

More questions on Structure determination from reaction sequences