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NEET 2019 · ChemistryPrevious Year Question

An alkene A on reaction with then gives propanone and ethanal in equimolar ratio. Addition of to alkene A gives B as the major product. The structure of B is:

Answer: (C) (C) (2-chloro-2-methylbutane). Ozonolysis giving propanone and ethanal means the C=C was between these two fragments, so A is 2-methylbut-2-ene, .

  1. A.(A) (primary chloride)
  2. B.(B) (primary side-chain chloride)
  3. C.(C) (2-chloro-2-methylbutane)✓
  4. D.(D) (secondary chloride)

Correct Answer

(C) (C) (2-chloro-2-methylbutane)

Solution & Explanation

Ozonolysis giving propanone and ethanal means the C=C was between these two fragments, so A is 2-methylbut-2-ene, . adds by Markovnikov's rule: goes to the carbon (less substituted) and to the more substituted carbon, forming the more stable tertiary carbocation. The major product B is 2-chloro-2-methylbutane, .

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