ORGANIC REACTIONS FOR UNIT 5

H3CH2X --> CH3CH2NH2 Halogenoalkane --> Amine CH3CH2X --> CH3CH2CN Halogenoalkane --> Nitrile CH3CH2X --> CH2=CH2 Halogenoalkane --> Alkene CH2=CH2 --> CH3CH2X Alkene --> Halogenoalkane CH3CH2X --> CH3CH2OH Halogenoalkane --> Alcohol CH3CH2OH --> CH3CHO Alcohol --> Aldehyde CH3CH2OH --> CH3COOH Primary Alcohol --> Carboxylic Acid CH3COOH --> CH3CH2OH Carboxylic Acid --> Alcohol Heat the halogenoalkane in a sealed vessel with excess ammonia (NH3) Reflux with a solution of potassium cyanide dissolved in ethanol Reflux in potassium hydroxide dissolved in ethanol

React with a hydrogen halide

Reflux in potassium hydroxide dissolved in aqueous solution Distil with acidified potassium dichromate solution. (K2Cr2O7) Reflux with acidified potassium dichromate solution.(K2Cr2O7) React with lithium tetrahydridoaluminate (Lithium aluminium hydride) (LiAlH4) in dry ether

CH3CHO --> CH3CH2OH Aldehyde --> Alcohol

React with lithium tetrahydridoaluminate (Lithium aluminium hydride) (LiAlH4) in dry ether or sodium tetrahydridoborate (NaBH4) React with phosphorus pentachloride (PCl5)

CH3CH2OH --> CH3COCl Alcohol --> Acyl Chloride CH3COCl --> CH3CONH2 Acyl Chloride --> Amide CH3CH2OH --> CH3COOCH2CH3 Alcohol --> Ester CH3COOH --> CH3COOCH2CH3 Carboxylic Acid --> Ester CH3CH(OH)CH3 --> CH3COCH3 Secondary Alcohol --> Ketone Benzene --> Nitrobenzene

React with ammonia (HN3)

Reflux with ethanoic acid and a strong acid catalyst (e.g. Conc H2SO4) Reflux with ethanol and a strong acid catalyst (e.g. Conc H2SO4) Reflux with acidified potassium dichromate solution.(K2Cr2O7) React with Conc Nitric acid and Conc Sulphuric acid below 55oC React with tin and hydrochloric acid

Nitrobenzene --> Phenylamine

Phenylamine --> Benzenediazonium chloride

React with nitrous acid (sodium nitrite and hydrochloric acid) React with acyl chloride and aluminium chloride

Benzene --> Phenylketone

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 React with bromine and uv light

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

Benzene --> Benzenesulfonic acid

React with fuming sulfuric acid (which is conc H2SO4 with additional SO3) 2,4,6-tribromophenol + HBr

Phenol + bromine water --> ?

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

Hunsdiecker Reaction

CH3CH2CN --> CH3CH2COOH

Reflux with dilute hydrochloric acid

CH3CH2CN --> CH3CH2CH2NH2

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