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Carbonyls
Aldehydes and Ketones
N Goalby
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C
H
H
H
CH3CHO
ethanal
If the C=O is on the end of
the chain with an H
attached it is an aldehyde.
The name will end in al
CH3COCH3
propanone
If the C=O is in the
middle of the chain it
is a ketone
The name will end in
-one
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Solubility in water
The smaller carbonyls are
soluble in water because they
can form hydrogen bonds with
water.
CH3
O
CH3
H3C
+ H2O
OH
OH
Reactions of carbonyls
In comparison to the C=C bond in alkenes, the C=O is
stronger and does not undergo addition reactions easily.
The C=O bond is polarised because
O is more electronegative than
carbon. The positive carbon atom
attracts nucleophiles.
- O
+ C
H3C
CH3
nucleophile
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Reaction 1: Oxidation
Revision of module 2
Primary alcohol
aldehydes
Secondary alcohol
carboxylic acid
ketones
Oxidation of Aldehydes
Reagents: Sodium dichromate and sulphuric acid
Conditions : heat under reflux
RCHO + [O]
RCO2H
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Blue
solution
red
precipitate
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LiAlH4
H
LiAlH4 must
be used in
anhydrous
conditions
propanone
Propan-2-ol
Reagents NaBH4
Primary alcohol
CH3CHO + 2[H]
Ketone
CH3CH2OH
primary
alcohol
CH3CH(OH)CH3
secondary
alcohol
Secondary alcohol
CH3COCH3 + 2[H]
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O
H3C
O:
H3C
CH3
H+
H3C
C
H
CH3
OH
C
CH3
propan-2-ol
Catalytic Hydrogenation
Carbonyls can also be reduced using catalytic hydrogenation
Reagent: hydrogen and nickel catalyst
Conditions: high pressure
Example Equations
CH3CHO + H2
CH3COCH3 + H2
CH3CH2OH
CH3CH(OH)CH3
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Room temperature
Equations
RCOR
+ HCN
RC(OH)(CN)R
RCH(OH)CN
RCHO + HCN
NC
OH
hydroxynitrile
CH3C(OH)(CN)CH3
CH3
CN
H3C
C N
H3C
CN
H3C
OH
C
CN
2-hydroxy-2-methylpropanenitrile
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H3C
..
H2N
NO 2
NH
addition
H3C
elimination of
water
O 2N
NH
NH
NO 2
O 2N
H3C
NO 2
NH
OH
Extra