Question

How can the following compounds be synthesized, starting with a hydrocarbon that has the same number of carbons as the desired product?

Short answer

Pent-1-ynereacts with R₂BH and OH^-, H₂O₂ and H₂O to form pentanal.

Step-by-step solution

Step 1:

Pent-1-ynereacts with R₂BH and OH^-, H₂O₂ and H₂O to form pentanal.

 

But-1-ene reacts with BH₂ and OH^-, H₂O₂and H₂O to form butan-1-ol.

Step 3:

The highest yield of desired ketone will come from this symmetrical alkyne.

The reaction does not require a mercuric ion catalyst because the reactant is not a terminal alkyne.