Benzyl chloride is the simplest side-chain halide.
Preparation of Benzyl Chloride.
(1) By passing chlorine into boiling toluene in the presence of UV light till the required increase in weight is reached.
(2) By the action of phosphorus pentachloride or thionyl chloride (SOCl2
) on benzyl alcohol.
Physical Properties Of Benzyl Chloride.
Benzyl chloride is a colourless unpleasant smelling liquid, bp 179C. it is vapours have irritating action on nose and eyes, causing flow of tears. It is insoluble in water but soluble in most organic solvents.
In the molecular orbital model of benzyl ion, the p orbitals of the Cl atom overlap with the available p orbitals of the benzene ring carbons. The extended molecular orbital has the positive charge of the benzyl ion distributed over all the seven carbons due to delocalization of electron. This makes the benzyl ion greatly stable.
Chemical Properties Of Benzyl Chloride.
is many times more reactive than alkyl halides. The increased reactivity of the chlorine atom is due to the ready formation of a stable carbonium ion.
The stability of the benzyl carbonium ion (C6
) arises from the distribution of the positive charge over the benzene ring due to resonance.
Benzyl chloride gives the following reactions:
(1) Nucleophilic Displacement Reactions. It undergoes nucleophilic displacement reactions like the alkyl halides.Thus,
(2) Wurtz Reaction. Upon treatment with sodium metal it gives bibenzyl (Cf: alkyl halides).
(3) Formation of Grignard Reagent.
(4) Oxidation. When treated with dilute nitric acid or alkaline potassium permanganate, the CH2Cl group is oxidised to COOH group, forming benzoic acid.
(5) Reduction. When reduced with Zn-Cu couple, it yields toluene.
(6) Electrophilic Aromatic Substitution. It gives the usual electrophilic substitution reactions of the benzene ring in ortho and para positions. For example.
Benzyl Chloride Uses.
Benzyl Chloride is used.
- For the manufacture of benzyl alcohol, benzylamine, and benzaldehyde.
- For introducing benzyl group in organic molecules.
Benzyl Chloride Structure.
Benzyl chloride, and α-chlorotoluene, is a organic compound. Benzyl chloride formula C₆H₅CH₂Cl and chemical formula is C7H7Cl.This is acolourless liquid is a reactive organochlorine compound that is a widely used in chemical building block.