Study Set Content:
Reactions take place between two carbonyl partners and involve a combination of nucleophilic addition and a-substitution steps.
Carbonyl Condensation Reactions
The nucleophilic donor is converted into an enolate ion and undergoes an
a-substitution reaction.
The electrophilic acceptor undergoes a
- nucleophilic addition reaction.
a base - catalyzed carbonyl condensation reaction undergone by aldehydes
and ketones with an a hydrogen atom undergo
Aldol
The B-hydroxy aldehydes and B-hydroxy ketones formed in aldol reactions are easily dehydrated to yield a,
B-unsaturated products, or conjugated enones
a hydrogen is abstracted and the resultant enolate ion expels the OH-leaving group in an ElcB reaction
Basic conditions
- an enol is formed, the -OH group is protonated, and H2O is then expelled in an El or E2 reaction.
Acidic conditions
- reaction between two ester molecules
Claisen Condensation Reaction
- an ester with an a hydrogen is treated with a base such as sodium ethoxide, a carbonyl condensation reaction occurs to yield a ẞ-keto ester.
Claisen Condensation Reaction
- sterilize surgical instruments, preservative for anatomical specimens because it causes skin hardening
Formaldehyde
- intermediate in the manufacture of acetic acid, ethyl acetate, vinyl acetate
Acetaldehyde
- Fragrant component of vanilla beans
Vanillin
- chief constituent of the oil of cinnamon bark
Cinnamaldehyde
- Major component of lemon grass oil
Citral
- Used as solvent for such products as paints, lacquers, and cellulose acetate because of its miscibility with both water and nonpolar solvents
Acetone
lacrimator and is used as a tear gas
Chloracetophenone
Nitrile
Hydrogen bond to themselves to form a
dimer
bonds have an effect on boiling poin
Hydrogen
- have higher boiling points
Carboxylic acids
