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benzal

Benzal chloride

Benzal chloride is an organic compound with the formula C6H5CHCl2. This colourless liquid is a lachrymator and is used as a building block in organic synthesis.

Benzal chloride is produced by the free radical chlorination of toluene, being preceded in the process by benzyl chloride and followed by benzotrichloride

C6H5CH3 + Cl2 → C6H5CH2Cl + HCl
C6H5CH2Cl + Cl2 → C6H5CHCl2 + HCl
C6H5CHCl2 + Cl2 → C6H5CCl3 + HCl

Most benzal chloride is hydrolysed to benzaldehyde:

C6H5CHCl2 + H2O → C6H5CHO + 2 HCl

Addition of strong base to benzal chloride generates phenylcarbene.

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