Organic Chemistry - Aldehydes and Ketones II: Enolates

Chapter 7 MCAT

alpha carbon

adjacent to the carbonyl carbon

alpha hydrogen

hydrogen connected to alpha carbon

Reactivity of aldehydes vs ketones

aldehydes slightly more reactive to nucleophiles than ketones,

enol

Presence of a carbon carbon double bond and an alcohol

Tautomers

two isomers, differ placement of a proton and double bond

Kinetic product

formed more rapidly but less stable

Thermodynamic product

formed more slowly but more stable

Conditions in which kinetic is favored

rapid, irreversible, low temps and strong sterically hindered base

Aldol condensation

the aldehyde or ketone acts as both nucleophile and electrophile resulting in aldol