Summary of Reaction Pathways in Organic Chemistry

SUMMARY OF REACTION PATHWAYS IN ORGANIC CHEMISTRY ALKANES

POLYALKENES

PRIMARY AMINES

ALKENES

DIHALOALKANES

ALKYL

HALOALKANES

EPOXYALKANES

HYDROGEN

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: n

C

C

C

C n

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: Br 2 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 Reagent: water  Conditions: warm Equation: C

C

+ H

alcohol

H2O

OSO3H

Type of reaction: hydrolysis 7.

Alkene alkane Reagent: hydrogen Conditions: 150 oC, Ni catalyst Equation: C

C

+

H

H

Type of reaction: hydrogenation

C

C

H

H

C

C

H

OH

+

H

OSO3H

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 O

Type of reaction: hydrolysis

11.

Haloalkane

alcohol

Reagent: NaOH(aq) or KOH(aq) Conditions: warm under reflux Equation: R-X + OH-  R-OH + XType of reaction: nucleophilic substitution 12.

Haloalkane nitrile Reagent: KCN in aqueous ethanol Conditions: boil under reflux Equation: R-X + CN-  R-CN + XType of reaction: nucleophilic substitution

13.

Haloalkane Amine Reagent: ammonia in ethanol in a sealed tube Conditions: heat Equation: R-X + 2NH3  R-NH2 + NH4X

HO

C

C

OH

Type of reaction: nucleophilic substitution 14.

Haloalkane alkene Reagent: KOH in ethanol Conditions: heat Equation: R

H

R

C

C

R

R

R C

X

R

+ X +

C

H2O

R

R

Type of reaction: elimination

15.

Primary alcohol aldehyde Reagent: potassium dichromate and dilute sulphuric ac id Conditions: warm, distillation Equation: RCH2OH + [O]  RCHO + H2O Type of reaction: mild oxidation

16.

Secondary alcohol ketone Reagent: potassium dichromate and dilute sulphuric ac id Conditions: heat, distillation Equation: R 1CH(OH)R 2 + [O]  R 1COR 2 + H2O Type of reaction: oxidation

17.

aldehyde carboxylic acid Reagent: potassium dichromate and dilute sulphuric ac id 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

OH Type of reaction: elimination 19.

glucose ethanol reagent: yeast conditions: 35 – 55 oC, no air  equation: C 6H12O6  2C2H5OH + 2CO2 type of reaction: fermentation

C

C

+

H2O