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JEE Advanced levelSingle correct optionDifficulty 3 of 3si274

The ketone shown is reduced with , the alcohol is dehydrated with hot conc. (Saytzeff product, ignore E/Z), and the alkene is subjected to reductive ozonolysis. How many different organic compounds are formed in the last step?

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

Answer: A

Butan-2-one is reduced to butan-2-ol, which dehydrates to the more substituted alkene, but-2-ene. Its reductive ozonolysis gives two molecules of the same product, ethanal, so only 1 compound. (But-1-ene, the minor alkene, would give two.)
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