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It reacts with water to produce hydrochloric acid and benzoic acid: C 6 H 5 COCl + H 2 O → C 6 H 5 COOH + HCl. Benzoyl chloride is a typical acyl chloride. It reacts with alcohols to give the corresponding esters. Similarly, it reacts with amines to give the amide. [5] [6]
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. Thus, benzyl chloride is a lachrymator and has been used in chemical warfare. It is also very ...
synthesis of benzamide from benzoyl chloride and a phenethylamine; synthesis of flutamide, a nonsteroidal antiandrogen; acylation of a benzylamine with acetyl chloride (acetic anhydride is an alternative) In the Fischer peptide synthesis (Emil Fischer, 1903), [6] an α-chloro acid chloride is condensed with the ester of an amino acid.
C 6 H 5 OH + NaOH → C 6 H 5 ONa + H 2 O. When a mixture of phenol and benzoyl chloride are shaken in presence of dilute sodium hydroxide solution, phenyl benzoate is formed. This is an example of the Schotten–Baumann reaction: C 6 H 5 COCl + HOC 6 H 5 → C 6 H 5 CO 2 C 6 H 5 + HCl
The benzoyl group is often abbreviated "Bz" (not to be confused with "Bn," which is used for benzyl), thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula – C 6 H 5 CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.
However, if an unreactive alkylating agent is used (e.g. an alkyl chloride) then the rate of reaction can be greatly improved by the addition of a catalytic quantity of a soluble iodide salt (which undergoes halide exchange with the chloride to yield a much more reactive iodide, a variant of the Finkelstein reaction).
While nucleophilic acyl substitution reactions can be base-catalyzed, the reaction will not occur if the leaving group is a stronger base than the nucleophile (i.e. the leaving group must have a higher pK a than the nucleophile). Unlike acid-catalyzed processes, both the nucleophile and the leaving group exist as anions under basic conditions.
In other chemical reactions, benzotrichloride reacts at the chlorinated α-carbon, for example in substitution reactions. It is used as an intermediate in the synthesis of benzoyl chloride, benzotrifluoride and 2,4-dihydroxybenzophenone which in turn are also intermediates in other reactions: [2] C 6 H 5 CCl 3 + resorcinol → 2,4 ...