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Chapter 18 Carbonyl Compound SMK Sacred Heart, Sibu

1. Preparation of carbonyl compound


Remove H2
A)Oxidation of alcohol, by KMnO4/H+ C-OHC=O
Insert O btw C-H 1o alcohol RCHO
Remove H2 2o alcohol RCOR
B) Dehydrogenation of alcohol, by Cu, 300oC
C-OHC=O
C) Ozonolysis of alkene, O3, Zn/H + *To avoid obtaining a
mixture of aldehyde and
ketone, the alkene must
be symmetrical

2. Reactions of carbonyl compound : ROCAig

R Reduction of C=O bond (i) LiAlH4 in dry ether, (ii) H3O+,


C=O C-O Na in C2H5OH
Insert H btw C-O H2, Ni, 180oC ,(Not suitable for aromatic compounds)
Insert H to empty bond
(i)NaBH4, ethanol (ii)H3O+, (For aldehyde & ketone)

O Oxidation (Aldehyde undergoes oxidation but not ketone) Insert O btw C-H
H+ RCOOH
KMnO4 / H+ OH- RCOO-
Cu2+ , OH- RCOO- , Cu2O (brick red ppt)
[Ag(NH3)2]+ , OH- RCOO- , NH3, Ag (mirror)

C Condensation by 2,4 - DNP + H2O

A Nu- addition (HCN in NaOH, NaCN as catalyst, pH 9-10, 10-20oC)

H2, Ni, 180oC


CH2NH2

H 3O + ,
COOH

i Iodoform test, I2 in NaOH,

RMgX + H2C=O
Meta
g Reaction of Grignard reagent RMgX + RCH=O
director
RMgX + RRC=O