reactants and conditions

PDC:

PDC

TPAP-NMO:

trace TPAP, NMO, anhydrous

Swern oxidation:

DMSO, -78*C

Jones oxidation:

CrO3, H2SO4

Pinnick oxidation:

NaClO2, NaH2PO4, 2,3-dimethylbut-2-ene to scavenge reactive HOCl product

Formation of acetals:

excess alcohol and anhydrous conditions push towards acetal

breaking down acetal:

excess water and acid pushes back to re-form ketone

Iminium ion formation:

primary amine, aldehyde/ketone, acid catalyst, anhydrous conditions

Reductive amination:

iminium ion, H+, Na(OAc)3BH as weak reducing agent

Elimination of HX from alkane/alkene:

LDA

Terminal alkyne to internal alkyne:

Na+NH2- (strong base), R-I

Reduction alkyne to alkane:

H2 and Pd-C

Reduction alkyne to Z-isomer:

H2 and Lindlar’s catalyst

Reduction alkyne to E-isomer:

Na dissolved in NH3

Wittig reaction:

Phosphorus ylid

Addition of water across alkene:

H2O, acid catalyst

Oxymercuration of alkene:

Hg(OAc)2, H2O, NaBH4

Hydroboration of alkene:

Organoborane, then H2O2, NaOH (oxidation of borane to OH)

Dihydroxylation of alkene:

trace OsO4, NMO, then H2O to remove Os and form diol

Ozonolysis of alkene:

O3, DCM solvent, then reducing agent (PPh3, Me2S, Zn and H+)

Alternative ozonolysis of alkene:

O3, DCM solvent, then oxidising agent to turn aldehydes to acids

Epoxidation of alkene:

Peracid (mCPBA), then nucleophile to open ring via SN2

Oxymercuration of alkyne:

Hg(OAc)2, H2O, H2SO4 (for tautomerisation)

Hydroboration-oxidation of alkyne:

Organoborane, H2O2, NaOH

Deprotonation of alkyne:

Organometal (NaNH2, BuLi, NaH), electrophile

Friedel-Crafts acylation:

AlCl3 or FeBr3

Electrophilic aromatic substitution:

Electrophile, base

Halogenation:

AlCl3 or FeBr3, base

Friedel-Crafts alkylation:

AlCl3 or FeBr3, base

Carbonyl to alkyl (Wolf-Kishner reduction):

H2NNH2, KOH, heat

Formation of aniline from benzene:

H2SO4, HNO3, then reduction with Sn, HCl or Pd-C catalyst

amide formation:

amine + acid anhydride or acyl chloride

Diazotization of alanine:

NaNO2, HCl, 0*C

Benzene with alkyl to aldehyde/ketone:

IDX in DMSO/Ph-F solvent

Benzene with alkyl (with H on first substituent atom) to carboxylic acid:

KMnO4, heat

Benzene with alkyl to alkyl bromide:

NBS, heat

Sulfonation then de-sulfonation:

H2SO4, SO3, 100*C to add, then NaOH, then H2O, H2SO4, 200*C to remove

Ortholithiation for 1,2-disubstitution:

Bu-Li, electrophile (initial group must have lp within 3 bonds of ring)

Organolithium/Grignard reagents:

THF solvent while forming reagent, acidic work up at end of reaction

Reaction with NaBH4:

NaBH4, EtOH solvent, acidic work up

Reaction with LiAlH4:

LiAlH4, THF solvent

Reaction with DIBAL-H:

DIBAL-H, acidic work up

Reaction with DIBAL ester to aldehyde:

1 eq. DIBAL, -78*C, THF

Reaction with DIBAL ester to alcohol:

2 eq. DIBAL, 0*C or r.t., THF

Hydration in acidic conditions:

H+ and water

Hydration in basic conditions:

OH- first, then H+