CHEM1611 Organic Chemistry Reaction Summary

1
THIOESTER
H / Cr2O72
1. LiAlH4 2. H / H2O
1. LiAlH4 2. H / H2O
ALDEHYDE
CARBOXYLIC ACID
AMIDE
RS
dilute H H2O / D
ROH H / D
ROH / H
HYDROLYSIS
Xs of NH3 or 1 or 2 amine
HEMIACETAL
Xs of NH3 or 1 or 2 amine
1. LiAlH4 or NaBH4 2. H / H2O
SOCl2
dilute H H2O / D
Xs ROH H / D
ACID CHLORIDE
ACETAL
ROH
RCOOH
ESTER
ACID ANHYDRIDE
ROH
dilute H H2O / D
H Cr2O72
ROH / H
Xs of NH3 or 1 or 2 amine
KETONE
H Cr2O72
1. LiAlH4 or NaBH4 2. H / H2O
NaOH
No Rxn
AMINE
H / Cr2O72
HX
1 ALCOHOL
3 ALCOHOL
2 ALCOHOL
DIHALOALKANE
RX
DISULFIDE
NH2
Salt of Amine
X2 in CCl4
I2
Zn / H
ALKENE
NH3 or amine
THIOL
KOH in ethanol
H2 / Pd
HX in CCl4
H2O dilute H2SO4
conc. H2SO4
NaOH
HX
X2 UV light
ALKANE
THIOETHER
ALCOHOL
HALOALKANE
RS
KOH in H2O
RO
Mg in dry ether
H2O
NaNH2 in liquid NH3
ETHER
H2O
Xs H2 / Pd
Grignard RMgX
ALKOXIDE
RCC
ALKYNE
1. CO2 2. H / H2O
H2O
1. RCHO or RC(O)R 2. H / H2O
RX
Mg in dry ether
1. LiAlH4 2. H / H2O
ALCOHOL
CARBOXYLIC ACID
ETHER
HALOBENZENE
PhCR(OH)R
RX
BENZENE
H / Cr2O72
PHENOXIDE
PhCH(OH)R
X2 / FeX3
H / Cr2O72
HNO3 conc. H2SO4
BENZOIC ACID
1. LiAlH4 or NaBH4 2. H / H2O
H2O
NaOH
NITROBENZENE
H / Cr2O72
H / Cr2O72
PHENOL
PhC(O)R
PhCH2OH
1. NaNO2 / HCl 2. H2O
ANILINE
HC(O)Cl AlCl3
Sn / HCl
BENZALDEHYDE
1. LiAlH4 or NaBH4 2. H / H2O