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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc073

Compound P () gives propanone and propanal on ozonolysis with reductive work-up. P is treated with (i) in THF, (ii) to give Q, and Q is heated with concentrated to give R as the major alkene. R is

  1. A4-methylpent-1-ene
  2. B4-methylpent-2-ene
  3. C2-methylpent-1-ene
  4. D2-methylpent-2-ene

Answer: D

Propanone plus propanal means P is , 2-methylpent-2-ene. Hydroboration-oxidation puts OH on the less substituted carbon C-3, giving 2-methylpentan-3-ol, . Acid dehydration follows Saytzeff's rule (and a hydride shift leads to the same tertiary cation), giving the trisubstituted alkene 2-methylpent-2-ene as the major product.
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