Enolate Chemistry

Carboxylic acids, esters, amides

structures formed by breaking/forming new bonds

a functional group with double bond and OH group

-will only work if there is one acidic hydrogen and can be removed by a base- a H bound to alpha carbon (which is the carbon next to the carbonyl carbon)

Step one: add a strong acid to protonate carbonyl oxygen Step 2: water= weak base and removes one of the alpha hydrogens. double bond forms between alpha carbon and carbonyl carbon and pushes charge up to the oxygen to get rid of the positive charge

Step one: add strong base to acetone to attacks alpha hydrogen and forms the double bond between the alpha carbon and carbonyl carbon this puts neg charge on oxygen Step two: water (which is the OH protonated from NaOH) comes in and the O- becomes OH

• resonance 2. hydrogen bonding

double bond can go several places, but some are favored

formed quickly, but less stable. double bond on less substituted. low temperature formed, strong & bulky base

Double bond forms between carbonyl carbon and substituted carbon. High temperature, less quick, more stable. weaker and less bulky base

aldehyde or ketone condense to form adol

strong base removes alpha hydrogen to form enolate. A new carbon carbon bond is formed and oxygen is protonated. possible to remove alpha hydrogen to get a double bond and we get alpha beta unsaturated aldehyde (dehydration reaction)

enol is protonated and can attack carbonyl carbon of aldehyde to get aldol. can break down to the unsaturated

either the catalyzed product or the dehydrated product

can generate two different enolates if there are two alpha carbons. after dehydration, all together 4 different products

-can produce too many products when chemists do this, they begin with one ketone (make sure only one alpha carbon has hydrogens)

neucleophiles

electrophiles

Enolate attacks the beta carbon (can act as electrophile) of the alpha beta unsaturated aldehyde or ketone double carbon carbon bond removed and neg charge on carbonyl carbon then removed to make a “1,5”

michael product and turn into enolate. forms a cyclic structure. de hydration can result in the new carbon carbon double bond to form an alpha beta unsaturated aldehyde or ketone