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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3si272

The alkane shown is monobrominated with and light. Select all correct statements.

  1. AFour constitutionally different monobromoalkanes are possible.
  2. BThe tertiary bromide is the major product.
  3. CCounting configurational stereoisomers as separate products, five monobromo products are possible.
  4. DAll four constitutional monobromides are achiral.

Answer: A, B

The compound shown is 2-methylbutane. Four constitutional bromides result (1-bromo-3-methylbutane, 2-bromo-2-methylbutane, 2-bromo-3-methylbutane, 1-bromo-2-methylbutane). Bromine is highly selective for the weakest, tertiary C-H bond, so 2-bromo-2-methylbutane is major. Two of the four have a stereocentre (2 enantiomers each), so stereoisomers give products, not 5, and not all bromides are achiral.
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