Reagents

NaOH / KOH

Nucleophilic substitution

Provides OH⁻ to substitute halogens or other groups

NaOEt / EtOH

Elimination (E2)

Strong base, eliminates HX to form alkenes

NH₃ / RNH₂

Nucleophilic substitution

Replaces leaving groups with –NH₂ or alkylamines

KMnO₄

Strong oxidizer

Oxidizes alkenes → diols; side chains → carboxylic acids

CrO₃ / H₂SO₄ (Jones)

Alcohol oxidation

1° alcohol → carboxylic acid; 2° alcohol → ketone

PCC

Mild oxidation

1° alcohol → aldehyde (doesn't over-oxidize)

O₃ / Zn (Ozonolysis)

Alkene cleavage

Splits alkenes into aldehydes or ketones

LiAlH₄ (LAH)

Strong reducer

Reduces esters, acids, ketones, aldehydes to alcohols

NaBH₄

Milder reducer

Reduces ketones and aldehydes → alcohols

H₂ / Pd or Pt

Catalytic hydrogenation

Reduces alkenes and alkynes → alkanes

Na/NH₃ (liq)

Partial reduction of alkynes

Alkyne → trans-alkene

H₂ / Lindlar’s cat.

Partial reduction of alkynes

Alkyne → cis-alkene

RMgBr (Grignard)

Nucleophilic addition

Reacts with carbonyls → alcohols after workup

RLi

Strong nucleophile

Similar to Grignard but more reactive

Gilman reagent (R₂CuLi)

Coupling reactions

Replaces halides with R groups (mild C–C coupling)

HNO₃ + H₂SO₄

Nitration

Adds NO₂ to benzene

Cl₂ or Br₂ + FeCl₃/FeBr₃

Halogenation

Adds Cl or Br to benzene

R–Cl + AlCl₃

Friedel–Crafts Alkylation

Adds alkyl group to benzene

R–COCl + AlCl₃

Friedel–Crafts Acylation

Adds acyl group (–COR) to benzene

Tollens’ reagent (Ag⁺/NH₃)

Aldehyde test

Oxidizes aldehydes to acids, gives silver mirror

Br₂ in CCl₄

Alkene test

Decolorizes with alkenes (adds across double bond)

NaH / LDA

Strong bases

Deprotonates weak acids (used in enolate formation)