Reaction guide
Every key reaction drawn out — starting material, reagents over the arrow, product. Search by name or reagent, or filter by type. Part of the OChem study guide.
Markovnikov addition of H–X across C=C
Markovnikov addition of H–OH
Markovnikov alcohol, no rearrangement
Anti-Markovnikov, syn addition of H–OH
Anti addition of two halogens (halonium ion)
Anti addition of X and OH
Anti-Markovnikov H–Br (radical)
Syn addition of H–H → alkane
Alkene → epoxide (syn)
Adds two OH syn → cis diol
Cleaves C=C into carbonyls
Markovnikov twice → geminal dihalide
Markovnikov → methyl ketone (via enol)
Anti-Markovnikov → aldehyde
Alkyne → cis (Z) alkene
Alkyne → trans (E) alkene
Extend the chain at a terminal alkyne
Backside attack, inversion
Via carbocation, racemization
Anti-periplanar, one step, Zaitsev
Via carbocation → Zaitsev alkene
Make OH a good leaving group
OH → tosylate (great leaving group)
E1 loss of water → alkene
1° alcohol → aldehyde (stops there)
1° alcohol → carboxylic acid
Anti opening → 1,2-diol
Aldehyde/ketone → alcohol
Even acids/esters → alcohol
Adds R⁻ to a carbonyl (new C–C)
Stronger carbon nucleophile
Carbonyl → alkene
Protect a carbonyl as an acetal
Carbonyl + 1° amine → C=N imine
Carbonyl + 2° amine → enamine
Adds CN and OH across a carbonyl
Enolate + carbonyl → β-hydroxy carbonyl
Aldol + dehydration → enone/enal
Two esters → β-keto ester
Halogen on the α-carbon (via enol)
Acid + alcohol → ester (reversible)
Ester → carboxylate + alcohol
Acid chloride + amine → amide
Carbonyl + amine → amine
Puts a halogen on the ring (EAS)
Installs –NO2 (EAS)
Installs –SO3H (reversible, EAS)
Adds an alkyl group (EAS)
Adds an acyl group (ketone)
Ar–NO2 → aniline
Brominates the allylic position
Substitutes an alkane C–H
Concerted [4+2] → cyclohexene