SUBSTITUTION Very Important for Organic Synthesis Reactions

Reactions

Alkanes:

SUBSTITUTION – very important for organic synthesis reactions

To Haloalkanes using F2, Cl2, Br2, I2 only

eg. C3H8 + Cl2 ® C3H7Cl + HCl

propane 1-chloropropane or 2-chloropropane

Alkenes and Alkynes:

ADDITION – occur much faster than alkane rxn

1) To Alkanes - with H2 (Hydrogenation)

eg. + H2 ®

ethene ethane

2) To Haloalkanes

(i) with X2 (X = F, Cl, Br,I) (Halogenation)

eg. + Cl2 ®

ethene 1,2-dichloroethane

(ii) with HX (X = F, Cl, Br,I) (Hydrohalogenation)

eg. + HCl ®

ethene chloroethane

3) To Alcohols - with H2O (Hydration)

eg. + H2O ®

ethene ethanol

For Hydrohalogenation and Hydration, Markovnikov’s Rule must be applied.

·  This rule states that the “ene” carbon that has the most Hs will get the H from the H-X or H-OH.

·  best know as the “rich get richer”.

eg. + HCl ®

2-methylbut-2-ene 2-chloro-2-methylbutane

Haloalkanes:

SUBSTITUTION

1) To Alcohols - with H2O

eg. + H2O ® + HCl

1-chloropropane propan-1-ol

2) To Amines - with NH3

eg. + NH3 ® + HCl

1-chloropropane 1-aminopropane

ELIMINATION

To Alkenes- using NaOH

eg. + NaOH ® + NaBr + H2O

2-bromopropane propene

Alcohols:

CONDENSATION

To Ethers - another alcohol

eg. + ®

butan-1-ol + propan-2-ol ® 1-(1-methylethoxy)butane

OXIDATION

1) To Aldehydes – using an Oxidizing agent, OA

eg. + Fe2O3 ® + FeO + H2O

butan-1-ol butanal

2) To Ketones – using and OA

eg. + FeO ® + Fe + H2O

butan-2-ol butanone

ELIMINATION

To Alkenes- using conc. acid as a catalyst

eg. ® + H2O

butan-2-ol but-1-ene

Ethers:

HYDRATION

To Alcohols - using conc. acid as a catalyst

eg. + H2O ® +

methoxyethane ethanol methanol

Ketones:

HYDROGENATION

To Alcohols- using H2

eg. + H2 ®

propanone propan-2-ol

Aldehydes:

OXIDATION

To Carboxylic Acids – using an Oxidizing agent, OA

eg. + CuO ® + H2O + Cu

propanal propanoic acid

HYDROGENATION

To Alcohols- using H2

eg. + H2 ®

propanal propan-1-ol

Carboxylic Acids:

CONDENSATION

1) To Esters – using an Alcohol (Esterification)

eg. + ® + H2O

propanoic acid ethanol ethyl propanoate

2) To Amides – using an Amine

eg. + ® + H2O

propanoic acid aminoethane N-ethyl propanamide