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JEE Advanced Chemistry Haloalkanes and Haloarenes 2023 JEE Advanced 2023 (Paper 2)

JEE Advanced Chemistry Question (2023) — Solution

Question

The reaction of 4 -methyloct- 1 -ene ( P , 2 . 52   g ) with HBr in the presence of C 6 H 5 CO 2 O 2  gives two isomeric bromides in a 9 :   1  ratio, with a combined yield of 50 % . Of these, the entire amount of the primary alkyl bromide was reacted with an appropriate amount of diethylamine followed by treatment with aq. K 2 CO 3  to give a non-ionic product S  in 100 % Yield. The mass (in mg ) of S obtained is [Use molar mass (in gmol - 1 ): H = 1 , C = 12 ,   N = 14 , Br = 80  ]

Options

  1. A. A
  2. B. B
  3. C. C
  4. D. D

Answer

A. A

Step-by-step solution

The 1-alkene undergo addition reaction and major product formed according to anti-Markonikov's rule. Moles of  P   = Mass   of   P Molar   mass   of   P = 2 . 52 252 = 0 . 01   mol Given that isomeric bromides formed have the mole fractions  9 10  and  1 10 Moles of  A (major product)  = 0 . 02 × 9 10 × 50 100 = 0 . 009   mol Now the alkyl bromide formed undergo nucleophilic substitution reaction with diethyl amine and potassium carbonate. In the above reaction, the product  S formed has the molecular weight  = 199   g   mol - 1 Mass of S = 0 . 009 × 199 = 1 . 791   g = 1791   mg

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