Carboxylic Acid --> Aldehyde
DiBal-H
Ester --> Aldehyde
DiBal-H
Nitrile --> aldehyde
DiBal-H
Carboxylic Acid --> primary alcohol
LiAlH4 or
BH3/THF
Acid Chloride --> primary alcohol
LiAlH4
Ester --> primary alcohol
LiAlH4
Anhydride --> primary alcohol
LiAlH4
Amide --> primary amine
LiAlH4
Nitrile--> primary amine
LiAlH4
Carboxylic Acid --> ester
Alcohol (R-OH/H+/heat)
1) SOCl2 2) alcohol/pyridine
CH2N2/diethyl ether
Acid Chloride --> ester
Alcohol (R-OH)
Transesterification
Ester and alcohol
Anhydride--> ester + alcohol
Alcohol (R-OH/H+/heat)
Carboxylic Acid--> acid chloride
SOCl2
Amide --> nitrile
SOCl2 + Heat
Lactone formation
Carboxylic acid and alcohol on same compound
H+/heat
Ester --> carboxylic acid
H3O+/heat (acid catalyzed)
1)OH-/H2O/heat 2) H3O+ (base catalyzed=saponification)
H2O (forms alcohol product too)
2 carboxylic acid --> anhydride
H3O+/heat
Aldehyde --> cyclic hemiacetal
H3O+/heat
Amino carboxylic acid --> lactan (cyclic amide)
H3O+/heat
Primary alcohol --> carboxylic acid
Jones (CrO3/H2SO4)
Secondary alcohol --> ketone
Jones
PCC
Alkyl Benzene --> carboxylic acid
Jones
KMnO4/HCl
Aldehyde --> carboxylic acid
Tollens
Ketone --> carboxylic acid
1) 3eq OH-/I2 2)OH-/H2O 3)HCl
CO2 --> carboxylic acid
R-MgX
Aldehyde --> secondary alcohol
R-MgX
Formaldehyde --> primary alcohol
R-MgX
Epoxide --> primary alcohol
R-MgX
Ketone --> tertiary alcohol
R-MgX
Nitrile--> ketone
R-MgX
Ester --> tertiary alcohol
2 eq R-MgX
2 eq CH3-Li/H3O+
Amide --> carboxylic acid
1) OH-/H2O/heat 2) H3O+ (base catalyzed)
H2O/H+/Heat (acid catalyzed)
Diketone --> cyclic conjugated ketone
intramolecular aldol
1) OH-/H2O/heat
2) H3O+
Aldehyde --> primary alcohol
NaBH4
Ketone --> secondary alcohol
NaBH4
Alkene --> alcohol
BH3 (least substituted)
Alkyne --> aldehyde
BH3
Acid Chloride --> primary amide
NH3
KCN --> primary nitrile
R-X
Acid chloride --> carboxylic acid
H2O
Nitrile --> carboxylic acid
H2O
forms imidic acid first then an amide then carboxylic acid + NH3
Anhydride --> 2 carboxylic acids
H2O
Ester --> amide
1) OH-/H2O/heat/HCl
2)SOCl2
3)NH3
Primary alcohol --> aldehyde
PCC
Aldehyde --> R-CH-N=H
NH3/H3O+
2 esters --> beta-keto ester
organic base (-OC2H5)/H3O+
diester --> cyclic beta-keto ester
-OC2H5/H3O+
2 ketones/aldehyde --> conjugated ketone/aldehyde
1) OH-/H2O
2) OH-/H2O/heat/H3O+
Diene + alkene --> cyclic alkene
hv
triene -->cyclic diene
hv
Acid chloride --> aldehyde
LiAlH (Ot-Bu)3
Carboxylic acid --> ketone
heat
decarboxylation
Primary amide --> primary amine
1)OH-/Br2
2) OH-/heat