Chemical properties
(i) Addition reaction: The carbonyl group is polar as oxygen is more electronegative than carbon,
Thus, the positive part of the polar reagent always goes to the carbonyl oxygen and negative part goes to carbonyl carbon.
However on reduction with sodium amalgam and water, it gives hydrobenzoin,
(ii) Clemmensen's reduction : With amalgamated zinc and conc. HCl, benzaldehyde is reduced to toluene.
(iii) Schiff's reaction: It restores pink colour to Schiff's reagent (aqueous solution of p-rosaniline hydrochloride decolourised by passing sulphur dioxide).
(iv) Tischenko reaction : On heating benzaldehyde with aluminium alkoxide (ethoxide) and a little of anhydrous AlCl3 or ZnCl2, it undergoes an intermolecular oxidation and reduction (like aliphatic aldehydes) to form acid and alcohol respectively as such and react to produce benzyl benzoate (an ester).
(v) Reactions in which benzaldehyde differs from aliphatic aldehydes
(a) With fehling's solution : No reaction
(b) Action of chlorine : Benzoyl chloride is formed when chlorine is passed through benzaldehyde at its boiling point in absence of halogen carrier. This is because in benzaldehyde there is no α-hydrogen atom present which could be replaced by chlorine.
(c) Cannizzaro's reaction : 
(d) Benzoin Condensation
(β-hydroxy ketone)
(e) Perkin's reaction
(f) Claisen condensation [Claisen-schmidt reaction]
(g) Knoevenagel reaction
(h) Reaction with aniline : Benzaldehyde reacts with aniline and forms Schiff's base
(i) Reformatsky reaction
(k) Reaction of benzene ring
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