SUMMARY OF REACTION PATHWAYS IN ORGANIC CHEMISTRY

ALKANES POLYALKENES
PRIMARY AMINES

ALKENES DIHALOALKANES

HALOALKANES ALKYL
HYDROGEN EPOXYALKANES DIOLS
SULPHATES

ALCOHOLS

NITRILES
CARBONYLS

CARBOXYLIC ACIDS

You need to know the equations, conditions, reagents and type of reaction for all these
reactions.

You need to know the mechanism for some of them.

1. Alkane  chloroalkane
reagents: Cl2
conditions: UV light
mechanism: free radical substitution
equation: RH + Cl2  RCl + HCl

2. Alkene  polyalkene
Conditions: low T, high p.
Equation:

C C
n C C

Type of reaction: addition polymerisation (free radical)

3. Alkene  bromoalkane
Reagent: HX(g)
Conditions: room T
Equation:

C C + H Br C C

Br H

Type of reaction: electrophilic addition

4. Alkene  dibromoalkane
Reagent: Br2 in water or in an organic solvent
Conditions: room T
Equation:

C C + Br Br C C

Br Br

Mechanism: electrophilic addition

5. Alkene  alkylhydrogensulphate
Reagent: concentrated sulphuric acid
Conditions: cold
Equation:

C C + H OSO3H C C

H OSO3H

Mechanism: electrophilic addition

6. Alkylhydrogensulphate  alcohol
Reagent: water
Conditions: warm
Equation:

C C
C C +
+ H2O H OSO3H
H OSO3H
H OH

Type of reaction: hydrolysis

7. Alkene  alkane
Reagent: hydrogen
Conditions: 150 oC, Ni catalyst
Equation:

H H C C
C C +
H H

Type of reaction: hydrogenation

8. Alkene  alcohol
Reagent: steam
Conditions: 300 oC, 60 atm, H3PO4 catalyst
Equation:
H H
C C + O C C

OH H

Type of reaction: hydration

9. Alkene  epoxyalkane
Reagent: oxygen
Conditions: 300 oC, silver catalyst
Equation:
O

C C + 1/2 O O C C

Type of reaction: oxidation

10. Epoxyalkane  diol

Reagent: water
Conditions: 60 oC, H2SO4 catalyst
Equation:
O

C C + H H HO C C OH
O

Type of reaction: hydrolysis

11. Haloalkane  alcohol

Reagent: NaOH(aq) or KOH(aq)
Conditions: warm under reflux
Equation: R-X + OH-  R-OH + X-
Type of reaction: nucleophilic substitution

12. Haloalkane  nitrile

Reagent: KCN in aqueous ethanol
Conditions: boil under reflux
Equation: R-X + CN-  R-CN + X-
Type of reaction: nucleophilic substitution

13. Haloalkane  Amine

Reagent: ammonia in ethanol in a sealed tube
Conditions: heat
Equation: R-X + 2NH3  R-NH2 + NH4X
Type of reaction: nucleophilic substitution
14. Haloalkane  alkene
Reagent: KOH in ethanol
Conditions: heat
Equation:
H R R R

C C -
R C C X + X + H2O
R R
R R
Type of reaction: elimination

15. Primary alcohol  aldehyde

Reagent: potassium dichromate and dilute sulphuric acid
Conditions: warm, distillation
Equation: RCH2OH + [O]  RCHO + H2O
Type of reaction: mild oxidation

16. Secondary alcohol  ketone

Reagent: potassium dichromate and dilute sulphuric acid
Conditions: heat, distillation
Equation: R1CH(OH)R2 + [O]  R1COR2 + H2O
Type of reaction: oxidation

17. aldehyde  carboxylic acid

Reagent: potassium dichromate and dilute sulphuric acid
Conditions: heat, reflux
Equation: R-CHO + [O]  R-COOH
Type of reaction: oxidation

18. Alcohols  alkenes

Reagent: concentrated sulphuric acid
Conditions: heat
Equation:

C C H C C + H2O

OH
Type of reaction: elimination

19. glucose  ethanol

reagent: yeast
conditions: 35 – 55 oC, no air
equation: C6H12O6  2C2H5OH + 2CO2
type of reaction: fermentation