Aldehyde & Ketone Reactions

Oxidation of primary alcohol to aldehyde

1^o Primary alcohol + PCC or Swern → aldehyde

Ozonolysis of alkenes

Alkene + O3 → aldehydes and/or ketones after workup

Friedel-Crafts acylation

Benzene + RCOCl/AlCl3 → aryl ketone

Hydration of alkyne (Markovnikov)

Internal Alkyne + H2SO4/Hg2+ → ketone via enol tautomerization

Hydroboration-oxidation of alkyne

Terminal alkyne + BH3/H2O2 → aldehyde (anti-Markovnikov)

Nitrile to ketone

Nitrile + RMgX then H3O+ → ketone

DIBAL-H reduction of nitrile

Nitrile + DIBAL-H → aldehyde

Acid chloride to aldehyde

Acid chloride + LiAlH(OtBu)3 → aldehyde

Acid chloride to ketone

Acid chloride + R2CuLi → ketone

Nucleophilic addition to carbonyl

Nucleophile attacks C=O → alcohol after protonation

Hydration of carbonyl

Aldehyde/ketone + H2O → geminal diol

Cyanohydrin formation

Carbonyl + HCN → cyanohydrin

Imine formation

Carbonyl + primary 1^o amine → imine (C=N)

Acetal formation

Carbonyl + ROH/H+ → acetal (protecting group)

Acetal hydrolysis

Acetal + H3O+ → carbonyl

Wittig reaction

Carbonyl + phosphonium ylide (Ph₃P=CHCH₃)→ alkene

Oxidation of aldehyde

Ag₂O/H₂O

Aldehyde → carboxylic acid

Tollens test

Aldehyde + Ag(NH3)2+ → Carboxylic Acid

NaBH4 reduction

Aldehyde/ketone + NaBH4 → alcohol

LiAlH4 reduction

Carbonyl + LiAlH4 → alcohol (strong reducer)

Catalytic hydrogenation

Carbonyl + H2/metal → adds alcohol (removes double bond and carbonyl)

Clemmensen reduction

Carbonyl + Zn(Hg)/HCl → alkane

Wolff-Kishner reduction

Carbonyl + NH2NH2/KOH → alkane

Acetal protecting group

Carbonyl + diol → cyclic acetal (protect)

Deprotection of acetal

Cyclic acetal + acid → carbonyl restored