CATALYTIC HYDROGENATION Ni HEAT CCl4

HALOGENATION DIHALOALKANE
ALKANE ALKENE

HYDROHALOGENATION DEHYDRATION H2O HALOHYDRIN

HYDRATION
FREE RADICAL ELECTROPHILIC ELIMINATION RXN
SUSBSTITUTION ADDITION RXN
ELECTROPHILIC
CONC H2SO4
MARKONIKOV’S RULE ELIMINATION RXN ADDITION RXN
UV light
SAYTZEFF’S RULE KETONE
DEHYDROHALOGANATION H3PO4, HEAT
Cl2 / Br2 KMnO4 /H+
SAYTZEFF’S RULE MARKONIKOV’S RULE
OXIDATION RXN
NaBH4

REDUCTION RXN

NUCLEOPHILIC HALOGEN HALIDE INORGANIC HALIDES

HALO
SUBSTITUTION @ HCl @ PCl5 2o
ALKANE
PCC in DCM
ALCOHOL CYANO
NUCLEOPHILIC NaOH OXIDATION RXN + HCN
REFLUX 1o HYDRIN
SUBSTITUTION (in aqueous)
KMnO4/H+

+
Mg REDUCTION RXN
CH2O

DRY ETHER NaBH4

DRY ETHER
NUCLEOPHILIC H3O+ REDUCTION RXN LiAlH4 H3O+ ALDEHYDE
SUBSTITUTION GRIGNARD CARBOXYLIC
REAGENTS ACID
KCN (in ethanol)
OXIDATION RXN KMnO4/H+
CO2 H3O+
DRY ETHER
CONC H2SO4
NITRILE SOCl2

DRY ETHER NH3

ESTER ACYL
CHLORIDE AMIDE
H3O+
 TESTING OF ALCOHOL

1. Lucas test
- 30 alcohol – cloudy immediately
- 20 alcohol – cloudy in 5 min
- 10 alcohol – no cloudiness
TESTING OF ALKENE
2. Oxidation KMnO4
1. Br2 in inert solvent or dilute bromine water - 10 & 20 alcohol – Purple to colorless
- Brown to colorless - 30 alcohol – no change
- alkene (in inert solvent) → dihaloalkane
- Alkene (Br2 water) → halohydrin 3. Iodoform
- Positive results for methyl alcohol & ethanol
2. Cold, dilute, alkaline KMnO4 (Baeyer’s test) - Pale yellow solid
- Purple to brown ppt
- Alkene → diol
TESTING OF CARBONYL
3. Hot, acidified KMnO4
- Purple to colorless 1. Brady’s reagent
10 C – CO2 - 2,4-dinitropehylhydrazine (2,4-DNP)
20 C – COOH - Turns to yellow-orange ppt
30 C – KETONE
2. Tollen’s reagent (silver mirror test)
- Positive results against aldehyde → silver mirror

3. Fehling’s reagent
- Positive result against aldehyde
- Deep blue → brick red

4. Iodoform
- Positive results for ethanal & methyl ketone
- Pale yellow solid