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The benzyl cation or phenylcarbenium ion is the carbocation with formula C 6 H 5 CH + 2; the benzyl anion or phenylmethanide ion is the carbanion with the formula C 6 H 5 CH − 2. None of these species can be formed in significant amounts in the solution phase under normal conditions, but they are useful referents for discussion of reaction ...
The benzyl alcohol thus formed is quickly converted to the chloride under the reaction conditions. Mechanism of Blanc chloromethylation Other possibilities for the electrophile include (chloromethyl)oxonium cation (ClH 2 C–OH 2 + ) or chlorocarbenium cation (ClCH 2 + ), which may be formed in the presence of zinc chloride. [ 4 ]
Benzyl chloride is an alkylating agent. Indicative of its high reactivity (relative to alkyl chlorides), benzyl chloride slowly reacts with water in a hydrolysis reaction to form benzyl alcohol and hydrochloric acid. In contact with mucous membranes, hydrolysis produces hydrochloric acid.
Benzyl alcohol is used effectively for treating lice infestations as the active ingredient in lotion shampoo with 5% benzyl alcohol. [ 13 ] Benzyl alcohol is an ingredient used in the manufacture of soaps, topical creams, skin lotions, shampoos, and facial cleansers and is popular due to its anti-bacterial and anti-fungal properties.
Benzyl bromide is used in organic synthesis for the introduction of the benzyl groups when the less expensive benzyl chloride is insufficiently reactive. [6] [7] Benzylations are often achieved in the presence of catalytic amounts of sodium iodide, which generates the more reactive benzyl iodide in situ. [3]
Benzylamine, also known as phenylmethylamine, is an organic chemical compound with the condensed structural formula C 6 H 5 CH 2 NH 2 (sometimes abbreviated as PhCH 2 NH 2 or BnNH 2).It consists of a benzyl group, C 6 H 5 CH 2, attached to an amine functional group, NH 2.
Typically these reactions would be conducted in the presence of a base which serves to absorb the HCl. Alkyl chloroformate esters degrate to give the alkyl chloride, with retention of configuration: ROC(O)Cl ' → RCl + CO 2. The reaction is proposed to proceed via a substitution nucleophilic internal mechanism. [3]
The effect of this for fluorobenzene at the para position is reactivity that is comparable to (or even higher than) that of benzene. Because inductive effects depends strongly on proximity, the meta and ortho positions of fluorobenzene are considerably less reactive than benzene.