Problem: Provide an appropriate alkyne starting material A and intermediate product beta. Omit byproducts. The number of carbon atoms in the starting material should be the same as in the final product.

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Hydroboration-Oxidation

  • Step 1: Alkyne + R2BH/THF → syn addition (anti-Markovnikov) 
    • regioselective Hydroboration
  • Step 2: Alkene—BR2 + H2O2 /NaOH/ H2O →  enol → enol-keto tautomerization → carbonyl (C=O) product
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Problem Details

Provide an appropriate alkyne starting material A and intermediate product beta. Omit byproducts. The number of carbon atoms in the starting material should be the same as in the final product.