Vinyl chloride

Vinyl chloride

The simplest unsaturated alcohol is vinyl alcohol, CH2=CHOH. This is, however, unknown; all attempts to prepare it result in the formation of acetaldehyde (together with a small amount of ethylene oxide), e.g., vinyl bromide on treatment with silver oxide in boiling water gives acetaldehyde.

CH2=CHBr  +  ‘AgOH’     AgBr  +  [CH2=CHOH]     CH3CHO

Although vinyl alcohol itself is unknown, many of its derivatives have been prepared, and are quite stable. These derivatives may be prepared by the interaction between acetylene and the other reactant in the presence of a suitable catalyst. e.g., vinyl chloride:

C2H2   +   HCl    (Hg2+)    CH2=CHCl

Vinyl chloride is manufactured by the thermal decomposition of ethylene dichloride at 600-650oC:

ClCH2CH2Cl        CH2=CHCl    +    HCl

Vinyl chloride and bromide are conveniently prepared in the laboratory by heating ethylene dichloride and dibromide, respectively, with ethanolic potassium hydroxide:

BrCH2CH2Br   +   KOH    (ethanol)     CH2=CHBr   +   KBr   +   H2O

Many of the vinyl compounds are used to make plastics. Vinyon, which is a thermoplastic, is a copolymer of vinyl chloride and vinyl acetate.

The halogen atom in vinyl halides is not reactive; vinyl halides do not undergo the usual double decomposition reactions of the alkyl halides. Vinyl chlorides and bromides readily form Grignard reagents in tetrahydrofuran as solvent and they react with lithium to form lithium compounds which undergo the usual reactions:

Vinyl chloride

The reaction for the unreactivity of the halogen atom is not clear. Some believe it is to be due to resonance through which the halogen atom acquires some double-bond character, and is thereby more strongly bound to the carbon atom due to the shortening of the C-CL bond:
Vinyl chloride


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