Two isomers A and B with Molar mass 184   g / mol and elemental compositio C ,   52 . 2 % ;  …

Two isomers A and B with Molar mass 184 g/mol and elemental compositio C, 52.2%; H, 49% and Br 42.9% gave benzoic acid and p- bromobenzoic acid, respectively on oxidation with KMnO4. Isomer 'A' is optically active and gives a pale yellow precipitate when warmed with alcoholic AgNO3. Isomer 'A' and 'B' are, respectively :
  1.  

  2.  

  3. H3C-CHBr-C6H5 and 

     

  4.  and H3C-CHBr-C6H5

Solution

Based on the percentage composition of the elements given the molecular formula of the compound is C8H9Br

And the degree of unsaturation or double bond equivalent of  C8H9Br is 4.

It is mentioned that A is optically active and gives pale yellow precipitate with AgNO3.

Hence, the structures of A and B can be deduced based on the following reactions.

 

Asked in: JEE Main 2022 (29 Jun Shift 2)

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