primary alcohol to aldehyde
PCC
terminal alkyne to aldehyde
1. BH3 2. H2O2, OH
terminal alkyne to ketone
HgSO4 and H3O+
ester to aldehyde
1. DIBAL-H 2. H3O+
acid chloride to ketone
R2CuLi
Oxidation of alkybenzene
KMnO4 or Na2Cr2O7
alkybenzene to benzoic acid
KMnO4 or Na2Cr2O7
Benzyllic bromination of alkybenzene
NBS, hv
Aryl Alkyl Ketone to alkybenzene
H2 Pd/C
Clemmenson Reduction
Zn(Hg), HCl
Wolff Kisshner reduction
NH2NH2, Oh
nitrobenzene to aniline
1. Fe, H3O+ 2. H2O or H2 Pd/C
Reduction of benzene ring
H2, Rh/C
aldehyde to carboxylic acid
KMnO4, Na2Cr2O7, CrO3 and H3O+, hot HNO3, Ag2O and NH4OH
Hydration of carbonyl to geminal diol
H2O and acid or base
aldehyde/ketone to acetal/ketal
2 ROH and H3O+
aldehyde/ketone to cayanohydrin
HCN
Cayanohydrin to primary amine
1. LiAlH4 2. H3O+
cayanohydrin to carboxylic acid
H3O+ and heat
aldehyde to 1 alcohol
1. NaBH4 or LiAlH4 2. H3O+
ketone to 2 alcohol
1. NaBH4 or LiAlH4 2. H3O+
aldehyde/ketone to alkane
NH2NH2, OH
alkybenzene to carboxylic acids
KMnO4
1 alcohol to carboxylic acid
CrO3 H3O+
aldehyde to carboxylic acid
CrO3 H3O+
nitrile acid catalyzed to carboxylic acid
H3O+ heat
nitrile base catalyzed to carboxylic acid
1. NaOH, H2O 2. H3O+
grinard Reagent to carboxylic acid
1. CO2 2. H3O+
1 alkyhalide to nitrile
NaCN
nitrile to primary amine
1. LiAlH4 2. H3O+
nitrile to ketone
1. RMgX 2. H3O+
carboxylic acid to acid chloride
SOCl2
2 Carboxylic acid and heat
acid anhydride
carboxylic acid to carboxylate anion
NaOH
carboxylate anion with a primary alkyl halide
Ester
Fisher Esterificiation
carboxylic acid to ester
carboxylic acid to ester
HCl and ROH
carboxylic acid to amide
DCC and RNH2
carboxylic acid to alcohol
1. LiAlH4 2. H3O+
carboxylic acid to alcohol
1. BH3 2. H3O+
carboxylic acid to acid chloride
SOCl2
carboxylic acid to acid halide
PBr3
acid halide to carboxylic acid
H2O
Conversion of acid halides into acid: Hydrolysis
H2O
acid halide and carboxylate anion
anhydride
acid halide into ester
primary alcohol and pyridine
acid chloride and 2 amines
Amides-aminolysis
acid chloride into alcohol
1. LiAlH4 2. H3O+
acid chlorides + 2 Grinard Reagents
alcohol
acid chloride + Gillman Reagents
Ketone
acid chloride with carboxylate anion
anhydrides
anhydrides into carboxylic acid
H2O
anhydride + alcohol
Ester
anhydride and amine
Amide
anhydride to alcohol
1. LiAlH4 2. H3O+
SN2 reaction of a carboxylate anion with a primary halide
ester
carboxylic acid to ester
add NaOH leads to carboxylate anion then primary halide leads to ester
Fischer esterification
carboxylic acid to ester
Fischer esterification carboxylic acid to ester
HCl and ROH
ester into carboxylic acid catalyzed
H3O+
ester into carboxylic acid base catalyzed
1. NaOH, OH 2. H3O+
ester into amide
NH3
Ester into alcohol
1. LiAlH4 2. H3O+
ester into aldehyde
1. DIBAL-H 2. H3O+
ester into tertiary alcohol
1. 2 RMgX 2. H3O+
acid catalyzed hydrolysis of amides into carboxylic acids
H3O+
base catalyzed hydrolysis of amide into carboxylic acids
1. NaOH, H2O 2. H3O+
Amides into amines
1. LiAlH4 2. H3O+
aldehyde/ketone and H2O
geminal diol (hydrate)
Geminal diol (hydrate) formation
aldehyde/ketone and H2O
Acetal formation
2 ROH and H3O+
aldehyde/ketone and primary amine
imine
aldehyde/ketone and secondary amine
enamine
aldehyde to primary alcohol
1. NaBH4 or LiAlH4 2. H3O+
ketone to secondary alcohol
1. NaBH4 or LiAlH4 2. H3O+
wolff-kishner reaction
aldehyde/ketone to alkane
aldehyde/ketone to alkane through wolff kishner reaction
NH2NH2 and OH-
conjugate addition 1,4 addition of amines
RNH2
conjugate addition 1,4 addition of water formation of B-hydroxy aldehyde and ketones
B-hydroxyl aldehyde/ketone
conjugate 1,4 addition of Gillman Reagent to a,B unsaturated aldehyde/ketone
1. R2CuLi 2. H3O+
Direct addition of Grignard Reagent
1. RMgX 2. H3O+
alkenes with one vinylic hydrogen oxidative cleavage
1. o3 2. zn and acetic acid
ozonolysis of alkene to yield a ketone
1.o3 2. zn/h3o+
aldehyde to carboxylic acid with tollen's reaction
Ag2o and NH4OH, h2O
reaction with water with aldehyde or ketones
geminal diols
nucleophilic addition of alcohols to form acetals
2ROH and HCl
aldehyde/ketone with HCN
cyanohydrin
nitrile to primary amine
1. LiAlH4 2. H3O+
nitrile to carboxylic acid
H3O+ and heat
nucleophilic addition of primary amine to ketone/aldehyde
imine
nucleophilic addition of secondary amine to ketone/aldehyde
enamines