Carbonyl compounds)
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VI.
A. 1.
Carbonyl compounds
Nucleophilic addition Reaction with hydrogen cyanide
O + HCN
R C R
O H
R C R
2.
R
H O C
SO3 Na
CH3/H
CH3/Hwhite precipitate
Note:
1. Sensitive to steric hinderance and reacts with aldehyde and methyl ketone only. 2. Can be used to purify aldehyde or methyl ketone.
B. 1.
Note : 1. A test for aldehyde or ketone. 2. Identify the carbonyl compound by characterization.
2.
H H H N N O2N
R NO2 R
2,4-dinitrophenylhydrazine
Note : 1. Test for aldehyde or ketone but no reaction with carboxylic acid and its derivatives 2. Identify the carbonyl compound by characterization.
3.
Triiodomethane formation
O H
R C C H
NaOH(aq) + I2(aq)
R
O
C + H
I
C I
H methyl ketone
C. 1.
[O] H R
O
C
OH
aldehyde
carboxylic acid
Note : Orange acidified potassium dichromate will turn to green chromium(III) ion.
2.
3.
R C O- + carboxylate ion
4.
5.
O
+ NaBH4(aq)
H3 O
R C R/H R/H
+
R
O
C
H
R/H
aldehyde or ketone O
+ LiAlH4(ether)
H alkoxide O
R C
H alcohol H3O
R/H
+
R
O
C
H
R/H
R/H
aldehyde or ketone
H alkoxide
H alcohol
6.
Haloform reaction
O H
R C C H
NaOH(aq) + I2(aq)
R
O
C + H
I
C I
H methyl ketone