Organic reactions made easy

H
H

SUBSTITUTION H C H + Br Br H C Br + H Br
Alkane → haloalkane H
H
Conditions: Heat OR sunlight Reactants: alkane + X2 (F, Cl, Br, I)
Type of substitution: halogenation Products: haloalkane + HX

REACTIONS OF OXIDATION 2C6H14 + 19O2 → 12CO2 + 14H2O

ALKANES (COMBUSTION) Alkane + oxygen → carbon dioxide + water + energy

H H H H H
H H H
H H
H C C C C C H H C C C H + C C
ELIMINATION H H H
H H
H H H H H
Alkane → alkene(s) +
alkane with shorter chain Type of elimination: (Thermal) cracking
Conditions: Heat + high pressure
Products: alkene(s) + alkane or alkene + H2

H H H H H H H H H H H
H H H C C C
+ HBr H C C C C H +/ H C C C C H
H H
H H C H
H H Br H H H H Br
C C + Cl Cl H C C H H Major product

H H
Cl Cl
Conditions: No water; Unreactive solvent
ADDITION

ADDITION

Conditions: Unreactive solvent Type of addition: hydrohalogenation

Type of addition: halogenation Reactants: alkene + HX (X = I, Br, Cl)
Reactants: alkene + X2 (X = Cl, Br) Product(s): haloalkane(s)
Product: haloalkane Major product: H atom attaches to the C atom
already having the greater number of H atoms

REACTIONS OF
ALKENES
H H H H H H H H H H H
ADDITION

ADDITION

H C C C
H H + H2O H C C C C H +/ H C C C C H
H H
Pt H H C H
H H OH H H H H OH
H Major product
C C + H H H C C H

H H H H
Conditions: Excess H2O; small amount of acid
Conditions: Pt, Pd or Ni as catalyst (H2SO4/H3PO4) as catalyst
Type of addition: hydrogenation Type of addition: hydration
Reactants: alkene + H2 Reactants: alkene + H2O
Product: Alkane Product: Alcohol(s)
Major product: H atom attaches to the C atom
already having the greater number of H atoms
 H H H H H H H H H H
heat
H C C C C H + Na OH H C C C C H + C C C C H + NaBr +H2O
H H H H H H H
H Br H H
major product

Conditions: concentrated strong base (NaOH, KOH, LiOH) + heat

Type of elimination: dehydrohalogenation
Reactants: Haloalkane + concentrated strong base Products: Alkene + NaBr + H2O
Major product: The one where the H atom is removed from the C atom with the least number of
H atoms (most substituted double bond forms i.e. double bond with most alkyl groups)

ELIMINATION
Haloalkane → alkene

REACTIONS OF HALOALKANES

SUBSTITUTION
Haloalkane → alcohol

H H H H H H H H H H H H H H H H

H C C C C H + Na OH H C C C C H + Na Br
H C C C C H + H2O H C C C C H + HBr

H H Br H H H OH H
H H Br H H H OH H

Conditions: Excess H2O + mild heat

Conditions: Dilute strong base (NaOH/KOH/LiOH) + mild heat
Type of substitution: hydrolysis
Type of substitution: hydrolysis
Reactants: Haloalkane + H2O
Reactants: Haloalkane + dilute strong base
Products: Alcohol + HBr
Products: Alcohol + NaBr/KBr/LiBr

H H H H H H H H H H H H H
H2SO4
H C C C C H H C C C C H + C C C C H + H2O
/ H
H C C H + HBr H C C H + H2O
H OH H H H H H H H H H
major product H OH H Br
Conditions: Dehydrating agent (H2SO4) + heat Conditions: Heat
Type of elimination: dehydration Reactants needed: Alcohol + HX
Reactants: Alcohol + H2SO4 Primary & secondary alcohols:
Products: Alkene(s) + H2O NaBr + H2SO4 used to make HBr in reaction flask
Major product: The one where the H atom is removed Tertiary alcohols: HBr (or HCl) directly
from the C atom with the least number of H atoms Products: Haloalkane + H2O

ELIMINATION SUBSTITUTION
Alcohol → alkene Alcohol → haloalkane

REACTIONS OF ALCOHOLS

ESTERIFICATION
Acid catalysed condensation

O H
H H H H
H O H H H H C C H
H C C C C O + H C C H2SO4 H C C C C O H + H2O
H O
H H H H H AlCl3 H H H H
H
Conditions: Acid as catalyst + heat
Reactants: Alcohol + carboxylic acid + H2SO4 Products: Ester + water