Unit 5 Organic Reactions

ORGANIC REACTIONS FOR UNIT 5 H3CH2X --> CH3CH2NH2

Heat the halogenoalkane in a sealed vessel with

Halogenoalkane --> Amine

excess ammonia (NH3)

CH3CH2X --> CH3CH2CN

Reflux with a solution of potassium cyanide dissolved

Halogenoalkane --> Nitrile

in ethanol

CH3CH2X --> CH2=CH2

Reflux in potassium hydroxide dissolved in ethanol

Halogenoalkane --> Alkene CH2=CH2-->CH3CH2X

React with a hydrogen halide

Alkene --> Halogenoalkane CH3CH2X -->CH3CH2OH

Reflux in potassium hydroxide dissolved in aqueous

Halogenoalkane --> Alcohol

solution

CH3CH2OH-->CH3CHO

Distil with acidified potassium dichromate solution.

Alcohol --> Aldehyde

(K2Cr2O7)

CH3CH2OH-->CH3COOH

Reflux with acidified potassium dichromate

Primary Alcohol --> Carboxylic Acid

solution.(K2Cr2O7)

CH3COOH-->CH3CH2OH

React with lithium tetrahydridoaluminate (Lithium

Carboxylic Acid --> Alcohol

aluminium hydride)(LiAlH4) in dry ether

CH3CHO-->CH3CH2OH

React with lithium tetrahydridoaluminate (Lithium

Aldehyde --> Alcohol

aluminium hydride)(LiAlH4) in dry ether orsodium tetrahydridoborate (NaBH4)

CH3CH2OH--> CH3COCl

React with phosphorus pentachloride (PCl5)

Alcohol --> Acyl Chloride CH3COCl-->CH3CONH2

React with ammonia (HN3)

Acyl Chloride --> Amide CH3CH2OH --> CH3COOCH2CH3

Reflux with ethanoic acid and a strong acid catalyst

Alcohol --> Ester

(e.g. Conc H2SO4)

CH3COOH -->CH3COOCH2CH3

Reflux with ethanol and a strong acid catalyst (e.g.

Carboxylic Acid --> Ester

Conc H2SO4)

CH3CH(OH)CH3 --> CH3COCH3

Reflux with acidified potassium dichromate

Secondary Alcohol --> Ketone

solution.(K2Cr2O7)

Benzene --> Nitrobenzene

React with Conc Nitric acid and Conc Sulphuric acid below 55oC

Nitrobenzene --> Phenylamine

React with tin and hydrochloric acid

Phenylamine --> Benzenediazonium chloride

React with nitrous acid (sodium nitrite and hydrochloric acid)

Benzene --> Phenylketone

React with acyl chloride and aluminium chloride

Benzene --> alkylbenzene

React with halogenoalkane and aluminium chloride

Benzene --> Bromobenzene

React with bromine and iron filings

Benzene --> cyclohexane

React with hydrogen in the presence of a Raney nickel catalyst at 150oC

Benzene --> 1,2,3,4,5,6-hexabromocyclohexane

React with bromine and uv light

Benzene --> Benzenesulfonic acid

React with fuming sulfuric acid (which is conc H2SO4 with additional SO3)

Phenol + bromine water --> ?

2,4,6-tribromophenol + HBr

CH3NH2 + CH3COCl --> ?

CH3CONHCH3

Adding a carbon atom to an organic molecule

R-X + KCN(alc) --> RCN + KX

Hoffmann's degradation

R-CONH2 + Br2 + 4KOH --> RNH2 ( +K2CO3 + 2KBr + 2H2O)

Hunsdiecker Reaction

RCOOAg + Br2 (Reflux in CCl4) --> RBr + CO2 + AgBr

CH3CH2CN --> CH3CH2COOH

Reflux with dilute hydrochloric acid

CH3CH2CN --> CH3CH2CH2NH2

React with lithium tetrahydridoaluminate (Lithium aluminium hydride)(LiAlH4) in dry ether