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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc245

The dibromide shown is treated with sodium in dry ether, and the organic product is examined by H NMR. How many signals does the product show?

  1. A1
  2. B2
  3. C3
  4. D4

Answer: B

The compound shown is 1,3-dibromo-2,2-dimethylpropane. Intramolecular Wurtz coupling joins the two carbons to give 1,1-dimethylcyclopropane. Its six methyl hydrogens are equivalent and its four ring hydrogens are equivalent, so there are 2 signals.
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