Type
Substitution
Family
Alkanes
Aromatics
(“m” form)
Alcohols
Addition
(start with
double bond)
Ethers
Making
Amines
Alkenes
Alkynes
Elimination
(produce
double bond)
Aldehydes
and
Ketones
Alcohols
Alkyl Halide
Reaction
Alkane + Halogen –(UV) haloalkane + Hydrogen
Halide
Benzene + H halide –(FeBr3 or AlCl3) Halobenzene +
H halide
Benzene + Alkyl Halide –(AlCl3) Alkyl benzene + H
halide
Benzene + Nitric Acid –(H2SO4) Nitrobenzene +
Water
Alcohol + H Halide –ZnCl2 (Lucas Reagent)  Alkyl
halide + H2O
Aldehydes
Alkyl attaches to benzene where
halide used to attach to it
Lucas Test:
1’ alcohol (2H’s): most soluble,
cloudy well after 5 minutes
2’ alcohol (1H): cloudy after 5
mins
3’ alcohol: Immediate cloudy
Ether + 2 Binary Acid –(Heat) 2 alkyl halides + H2O
Alkyl Halide + Ammonia  Amine + H halide
Alkene + H2 –(Pt) Alkane
2 reactants to 1 product
Alkene + Halogen –(CCl4) Haloalkane
Alkene + H Halide  Haloalkane
Haloalkane has 2 halogen atoms
Haloalkane has 1 halogen atom
H atom goes on C with more H
atoms, resulting in multiple
possibilities sometimes
CANNOT make primary alcohol
Alkene + H2O –(H2SO4 and 100C)  Alcohol
Same as alkenes but 2 moles of each to get alkane
Can’t use 1 mole to get alkane
Aldehyde + H2 –(Pt and 101 MPa) Primary alcohol
Ketone + H2 –(Pt and 101 MPa)  2’ alcohol
Alcohol –(H2SO4 and 100C)  Alkene + H2O
Also a reduction reaction
1 reactant to 2 products
Condition same as addition =
inefficient reaction
Alkyl Halide + OH-  Alkene + H2O + Halide ion
Oxidation
Alkenes
Alcohols
Notes
1 halogen mole for each halide
branch
Alkene –(OA) diol
1’ alcohol –(OA) Aldehyde –(OA) Carboxylic Acid
2’ alcohol –(OA) Ketone
3’ alcohol  No reaction
Aldehyde –(OA) Carboxylic Acid
Ketones cannot be oxidized
Oxidizing Agents (OA):
Cr2O72- (ornge)  Cr3+ (gren)
MnO4 (purp)  MnO2 (brwn)
Each C in x2 bond gets 1 OH
Can be used to detect diff
between 1’ and 2’ with 3’, but not
bet. 1’ and 2’
Distinguish bet. ald and ket
OA
Fehling’s Solution (Cu2+): blue to
copper colour in ald
Tollen’s Reagent (Ag+ in NH3):
clear to black precipitate with
silver coating on glassware
Condensatio
n
Alcohols
Alcohol + Alcohol –(H2SO4 and 140C) Ether + H2O
Amines
Amine + Carboxylic Acid –(H2SO4 and Heat) Amide + Only 1’ and 2’ amines
H2O
H from N, OH from carboxylic
acid
Amides + H2O –(H2SO4 and Heat) Amine + Carboxylic
Acid
Amides
VS Elimination: H and OH of
water come from different
molecules
Alcohol + Carboxylic Acid –(H2SO4 and Heat)  Ester + Esterification
H2O
H from hydroxide, OH from
carboxylic acid