Orgo aldehyde and ketone predicting product flashcards

Primary alcohol + PCC

Aldehyde

Primary alcohol + DMP

Aldehyde

Aldehyde + strong oxidizing agent

Carboxylic acid

Secondary alcohol + oxidation

Ketone

Ketone + strong oxidant (KMnO4, heat)

Cleavage to carboxylic acids

Aldehyde + NaBH4

Primary alcohol

Ketone + NaBH4

Secondary alcohol

Aldehyde/ketone + LiAlH4 then H3O+

Alcohol

Aldehyde + RMgX then H3O+

Secondary alcohol

Ketone + RMgX then H3O+

Tertiary alcohol

Carbonyl + nucleophile

Tetrahedral intermediate (sp2 to sp3)

Aldehyde/ketone + H2O (acid or base)

Geminal diol

Aldehyde/ketone + NaCN then H3O+

Cyanohydrin

Aldehyde/ketone + 1° amine (acid)

Imine

Aldehyde/ketone + 2° amine (acid)

Enamine

Aldehyde/ketone + 3° amine

No reaction

Aldehyde + 2 ROH (acid)

Acetal

Ketone + 2 ROH (acid)

Ketal

Acetal/ketal + H3O+

Aldehyde/ketone

Aldehyde/ketone + NH2NH2 + KOH + heat

Alkane (Wolff-Kishner)

Aldehyde/ketone + Wittig reagent

Alkene

α,β-unsaturated carbonyl + strong nucleophile (RMgX, H-)

1,2-addition (alcohol)

α,β-unsaturated carbonyl + weak nucleophile (CN-, RS-, amine)

1,4-addition (β-substituted carbonyl)

α,β-unsaturated carbonyl + RO- or HO- (basic)

1,4-addition

α,β-unsaturated carbonyl + ROH (acidic)

Acetal/Ketal