Draw the product of the given reaction sequence.

Question

Methyl vinyl ketone

3,4‑dihydrophenanthren‑1(2H)‑one ---------------------------------->

NaOCH3, CH3OH, heat

Answer 1

The given reaction sequence involves the use of sodium methoxide (NaOCH3), methanol (CH3OH), and heat to deprotonate and condense 3,4-dihydrophenanthren-1(2H)-one with methyl vinyl ketone. The product of this reaction sequence is a substituted dihydrophenanthrene derivative. Specifically, the methoxide ion (CH3O-) will deprotonate the alpha position of the ketone group in methyl vinyl ketone, creating an enolate ion. This enolate ion will then undergo nucleophilic addition to the carbonyl group of 3,4-dihydrophenanthren-1(2H)-one, forming a new carbon-carbon bond and generating an alkoxide intermediate. This intermediate will then undergo proton transfer and dehydration to form the final product. The exact structure of the substituted dihydrophenanthrene derivative formed will depend on the specific reaction conditions and the relative proportions of the reactants used.