Ch. 15 Aldehydes and Ketones Reactions

Nucleophilic Acyl Additions Reactions

Grignard Reagents, Organlithium reagents, Terminal alkyne anion, and Cyanide Ion

______ creates new chiral centers in aldehydes and ketones, if the starting materials are achiral, than it’s a ________ mixture

Grignard Reagents; racemic

Addition to Formaldehyde

Grignard + formaldehyde = primary OH

• acid work up as the second step

Addition to Aldehyde

Grignard + aldehydes = secondary OH

• acid work-up second step

Addition to Ketone

Grignard + ketone = tertiary OH

• acid work up second step

Alcohol Production via Organolithium Compounds

Organolithium + ketone = lithium alkoxide + acid work-up = alcohol at the carbonyl

• new C-C bond formed between the organometallic compound and the ketone

Addition of Terminal Alkyne Anions

nucleophilic alkyne + ketone = alkyne alkoxide + acid work-up → alcohol and alkyne product

Addition of Hydrogen Cyanide

Aldehyde + HCN → OH and triple bond C-N at the H

Wittig Reaction

1. Ph3 + CH3-I → Ph3-CH3

2. Ph3-CH3 + RCOR → Betaine (cyclic structure)

3. Betaine collapses → Ph3P=O + H2C=CR2