How is benzyl chloride prepared from toluene?

How is benzyl chloride prepared from toluene?

Preparation. Benzyl chloride is prepared industrially by the gas-phase photochemical reaction of toluene with chlorine: C6H5CH3 + Cl2 → C6H5CH2Cl + HCl. In this way, approximately 100,000 tonnes are produced annually.

What happens when toluene undergoes chlorination?

When toluene reacts with chlorine in the presence of ferric chloride it gives o-chlorotoluene and para-toluene and hydrochloride as the products. The major products formed in this reaction are o-chlorotoluene and p-chlorotoluene.

Which reagent is used in the chlorination of toluene?

The ZnnCl−2n+1 and AlnCl−3n+1 anion-containing ionic liquids with high Lewis acid strength favored the chlorination of toluene to chlorinated toluene via the electrophilic substitution reaction, suppressing the formation of benzyl chloride via the free radical reaction.

What is chlorination of toluene?

Hint: It is a two-step conversion question, chlorination is free-radical mechanism of adding chlorine radicals to the methyl group of toluene and then, addition of aqueous $\text{NaOH}$ is like hydrolysis of the chlorine atoms attached to the carbon atom.

How is toluene converted to benzyl alcohol?

The conversion of toluene to benzyl alcohol is a two-step procedure. Toluene is converted to benzyl chloride in the presence of chlorine gas and ultraviolet light or heat. Benzyl chloride then reacts with aqueous potassium hydroxide to give benzyl alcohol.

How do you convert benzyl chloride to benzyl alcohol?

Answer: The compound with a group -CH2Cl attached to the benzene ring is benzoyl chloride, and the compound with a group -CH2OH attached to the benzene ring is benzoyl alcohol. Benzyl chloride undergoes a substitution reaction when reacting with aqueous potassium hydroxide to give benzyl alcohol.

What happens when toluene is treated with chlorine in the presence of light?

When the reaction takes place in light the substitution occurs on the methyl group instead of benzene ring, hence 3 hydrogen of alkyl group het substituted by 3 hydrogen and trichloromethyl benzene forms.

What happens when toluene is treated with chlorine in presence of sunlight?

The reaction we are going to explore happens between methylbenzene and chlorine in the presence of ultraviolet light – typically sunlight. One of the hydrogen atoms in the methyl group has been replaced by a chlorine atom, so this is a substitution reaction.

How is toluene converted to O chlorotoluene?

o-Chlorotoluene as an important raw material has been widely used in the production of pharmaceuticals, pesticides, spices, and dyes [1–5]. o-Chlorotoluene has been commercially produced by the chlorination of toluene with gaseous chlorine over conventional Lewis acid catalysts, such as FeCl3 and AlCl3, accompanied by …

What is side chain chlorination of toluene?

Side chain chlorination of toluene gives dichloromethyl benzene. This on hydrolysis gives benzaldehyde.

What is the chemical formula of toluene?


How is benzyl chloride used in chlorination of toluene?

In electrochemical chlorination at optimum conditions, 81% of benzyl chloride and 9% of unconverted toluene was obtained after passing 3.5 F charge per mole of toluene. The curves in Fig. 1 shows the relative quantities of toluene, benzyl chloride as a function of charge passed on electrochemical chlorination of toluene.

How to make benzyl chloride with redistilled sulfuryl chloride?

In a 500ml round-bottomed flask, fitted with an efficient reflux condenser, place 92g (106 ml) of toluene, 68 g (41 ml) of redistilled sulfuryl chloride and 1 g of dibenzoyl peroxide. Reflux gently, when a vigorous reaction takes place: the reaction is complete in 30 minutes. Isolate the benzyl chloride as described in the method above.

How is the yield of benzyl chloride determined?

The yield of benzyl chloride is about 100 g. An alternative method of determining the completion of the reaction is to weigh the flask and toluene, and to stop the passage of chlorine when the increase in weight is 37 g. The benzyl chloride may also be isolated by distillation under atmospheric pressure.

What happens when benzyl alcohol is mixed with hydrochloric acid?

When the alcohol and a large excess of the acid were mixed, the reaction took place at the room temperature after a few minutes, and a theoretical yield of the chloride separated. Benzyl alcohol dissolves sparingly in hydrochloric acid of the specific gravity 1.12. when the solution is warmed, benzyl chloride is formed.

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