Alcohols & Esters Flashcards
Compare the boiling points of alcohols and esters
Alcohols have higher boiling points due to hydrogen bonding
How can oxymercuration be used to produce an alcohol?
Mercury acetate is added to an alkene to produce a hydroxyalkyl mercury compound, which then undergoes demercuration using NaBH4 to replace the acetoxymercury group with a hydrogen
How can hydroboration produce an alcohol?
An alkene reacts with BH3 to produce an alkylborane, which undergoes oxidation with hydrogen peroxide to yield the alcohol
How is Markovnikov or anti-Markovnikov addition determined?
Whether the nucleophile (such as -OH) was added to the most or least (anti) substituted group
Oxymercuration always leads to…
Markovnikov addition (most substituted)
Boronation always leads to…
anti-Markovnikov addition (least substituted)
Acid-catalyzed ring opening occurs at…
the most substituted carbon
Base-catalyzed ring opening occurs at…
the least substituted carbon