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If primary alcohol is oxidized, distill out the aldehyde immediately. But normally aldehyde is difficult to synthesize.
Anhy. AlCl3
R C O + HCl
Methanal is a gas, other lower members of aldehydes and ketones are liquids. Benzenecarbaldehyde is a colourless liquid with almond smell. Ethanal and propanone are miscible with water due to the formation of H-bond with water molecules while benzenecarbaldehyde is insoluble in water.
R.A.: 1. Can be H2 / Pt, Ni or Pd (also reduce C=C and CC) 2. Na/ Hg in ethanol (also reduce RX) 3. LiAlH4, NaBH4 (for LiAlH4, also reduce acid & acid derivative)
RCOONa
Cu2O
OH2
RCOONH4 + Ag + H2O
Tollens reagent is formed from silver nitrate solution and aq. ammonia This is called silver mirror test.
This reaction is not good method because you cannot control where the bond break.
I2, NaOH
I3C
I2, NaOH
O Na+
OH , H3C C H
Energy Profile
Reaction Coordinate
Nucleophilic Addition reaction (contd) Factors affecting reactivity: Electronic Factor Benzenecarbaldehyde has low reactivity due to the loss of resonance energy when attacked by nucleophile.
C H
NC
OH
HOOC
OH
cyanohydrin
+ O +H
CN
+ O H
NC
OH
On cooling, the bisulphite addition compound is crystallized. This reaction is a method for purification and separation of carbonyl compound (also identification). The carbonyl compound is regenerated by addition of alkali.
OR hemiacetal
OR C OR ketal R''
OR hemiketal
COO + C2H5OH
dry HCl
OH2 O O O O
COOC2H5
OH
COO + C2H5OH
From aldehyde, product is aldoxime From ketone, product is ketoxime They are white solids. The reaction can thus serve as a test for carbonyl compounds.
hydrazine
-hydrogen
H H2O + H3C C
H C
O C H
-hydrogen
HO
H C C OH C
O C H OH2 C
H C O C
O C H
H H C H
H C H
H C H C H C
O C H
warming
CH2CH3
Dismutation reaction (disproportionation) Benzaldehyde (with no -H) is oxidised, and at the same time, reduced.