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CHEMICAL PROPERTIES OF
ALDEHYDES AND KETONES
By:Takeen Khurshid
To: Dr. Geeta Durga
Aldehydes:
General formula:
RCHO or RCH=O
Ketones:
General formula:
RCOR’ (R and R’=alkyl or aryl)
Naming Of Aldehyde:
•Select the longest continuous carbon chain that contains the C=O group and replace
the ending by the suffix al.
•The CHO group is assigned the number 1 position and takes precedence over other
functional groups that may the present such as –OH, C=C.
Common name: listing the alkyl substituents attached to the carbonyl
group, followed by the word ketone.
IUPAC system: replace the ending –e by the suffix –one. The chain is
numbered in such a way as give the lowest number to the C=O group.
Common Dimethyl ketone Methyl phenyl ketone Methyl vinyl ketone Diphenyl ketone
Acetone Acetophenone Benzophenone
IUPAC Propanone Phenyl ethanone 3-Buten-2-one Diphenylmethanone
CH3 C CH3
O
CH3 C C6H5
O
CH3 C CH=CH2
O
H5C6 C
O
C6H5
Naming Of Ketone
 Because the polarity of the carbonyl group, aldehydes and ketones are
polar compounds.
 Dipole-dipole attractions, although important, are not as strong as
interactions due to hydrogen bonding. As a result, the boiling points of
aldehydes and ketones are higher than those of nonpolar alkanes, but
lower than those of alcohols.
 The lower aldehydes and ketones are soluble.
C O C
+
O
-
O
C O
C
δ
−
δ
−
δ
+
δ
+
C O H
O
H CO
δ
−
δ
+
δ
+
δ
−
C+δ
O-δ
H
H
C+δ
O-δ
H
R
C+δ
O-δ
R'
R
> >
Activity of the carbonyl group
C+δ
O-δNu-
C O-Nu
E+
C OENu
alkane alcohol
aldehyde
ketone
carboxylic acid
oxidation
reductionreduction
addition
productnucleophilic
addition
CHEMICAL
PROPERTIES:
Aldehydes & ketones, reactions:
1) Oxidation
2) Reduction
3) Addition of cyanide
4) Addition of derivatives of ammonia
5) Addition of alcohols
6) Condensation Reactions
7) Addition of Grignard reagents
8) (Alpha-halogenation of ketones)
9) Cannizzaro reaction
Aldehydes
and ketones
Alcohols
Lactones
and esters
Oximes
Amides
CyanohydrinsEnols and
enolate anions
Hydrazones
Alkenes
Alkanes
Ketals and thioketals Carboxyllic acids
1..Hydrate Formation
1- Reduction of carbonyl group
a- Addition of metal hydride
CH3
O
H
2 H2 / Pd
CH3
OH
CH3
OH
1) NaBH4
2) H2O
C O C O-M+H C OHH+ M+
H-
H2O
H+
H2O
H+
O
LiAlH4
OAl
H
OH
R C
O
H
R CH OH
R'
R C OH
R'
R''
R C R'
O
+ R'MgX
1) Dry ether
2) H2O
+ R''MgX
1) Dry ether
2) H2O
CH3 C
O
H
CH3 CH
OH
C2H5+ C2H5MgX
1) Dry ether
2) H2O
+ CH3MgX
1) Dry ether
2) H2O
O
CH3
OH
b- Addition of Grignard Reagents: Formation of alcohols
c- Clemmenson reduction
d- The Wolf-kishner reduction
O
COOH HCl / Zn(Hg) COOH
H
H
COOH
O
NH2NH2
COOH
N-NH2
COOH
NaOH
∆
H
H
e- Wittig reaction
C
O
+ CH2=P(C6H5)3
THF
C
O-
CH2
P(C6H5)3
C
O
CH2
P(C6H5)3
C CH2 + (C6H5)3P=O
H
O
+ (Ph)3P=CH C OC2H5
O
OC2H5
O
2- Oxidation reaction
a-
b- Tollenis test
c- Iodoform reaction
R-CHO or Ar-CHO
KMnO4
or K2Cr2O7
RCOOH or ArCOOH
RCOO-
+ 2 Ag(NH3)+
2 + OH-
+ 2 Ag + 4 NH3 + 3 H2ORCHO
C O
CH3
R
+ 3 I2 + 4 NaOH R
O
O
-
Na
+ + CHI3 + 3 NaI
CH3
CH3
O
I2 / NaOH
CH3
COONa
+ CHI3
R C OH
R'
CN
R C R'
O
+ HCN
O
H
+ HCN
OH
CN
Cyanohydrin
Benzaldehyde cyanohydrin
O
+ HCN
OH
CN
H2 / Pt
or LiAlH4 and H3O
+
OH
NH2
H3O
+
Heat
OH
COOH
3- Addition of Hydrogen Cyanide: Formation of cynohydrins
R C
O
R
2
R C OH
R'O
R
2
+ R'OH
CH3 C
O
H
CH3 CH
OH
OC2H5
+ C2H5OH
H
+ R''OH
H
+ R C OR''
R'O
R
2
R
2
=H:
R
2
=Alkyl
Aldehyde
Ketone
Hemiacetal
Hemiketal
Acetal
Ketal
H
+
C2H5OH
H
+
CH3 CH
H5C2O
OC2H5
Hemiacetal Acetal
CH3 C
O
CH3
CH3 C
OH
OC2H5
CH3
+ C2H5OH
H
+
C2H5OH
H
+
CH3 C
H5C2O
OC2H5
CH3
Hemiketal Ketal
4- Addition of alcohols:
C O
NH3
C NH
Imine
NH2OH
Hydroxylamine
C N OH
C N NH2
C N NH
C N NH
O2N
NO2
C N NH C NH2
O
Oxime
NH2 NH2
Hydrazine
Hydrazone
NH2 NH
Phenylhydrazone
Phenylhydrazine
NH2 NH
O2N NO2
2,4
-
Dinitrophenylhydrazone
NH2 NH C NH2
O
Semicarbazide
Semicarbazone
6- Addition of Ammonia and Ammonia Derivatives
7.ALDOL CONDENSATION
 Condensation between two molecules of an Aldehyde or a
ketone to form a β-hydroxyl aldehyde or a β-hydroxy ketone is
known as a ALDOL CONDENSATION.
 ALDOL CONDENSATION is possible only when the carbonyl
compound contains atleast one α-hydrogen atom.
MECHANISM
enolate
ion
An enolate ion is the anion formed when
an alpha hydrogen in the molecule of
an aldehyde or a ketone is removed as a
hydrogen ion.
The alkoxide ion is the conjugate
base of alcohols.
Alkoxide ion is protonated by water.
Crossed aldol condensation
In the presence of a strong base, two
different molecules of aldehyde or ketone
combine to form a β-hydroxyaldehyde or a
β-hydroxyketone.
This reaction is called as the aldol
condensation.
The enolate ion (carbanion) is the actual
nucleophilic reagent.
The reaction breaks down to the
following:
The α-carbon of the donor attaches itself to
the carbonyl carbon of the acceptor.
Step 1: Deprotonation and formation of
nucleophile.
• Step 2: Attack by nucleophile: Formation of alkoxide
ion.
 Step 3: Hydrolysis and formation of Aldol type product
Step 4: Intramolecular dehydration
8- Cannizzaro reaction
Aldehyde which does not contain α hydrogen undergoes Cannizzaro
reaction.
CHO
+ NaOH (30 %)
∆
+
CH2OH
COO-
Na+
CH
+ OH-
C
O-
OH
O
H
C
C CH2O-
+
OH
O
O
H
C CH2OH
+
O-
O
more stable anion
Aldehydes and ketones
Aldehydes and ketones

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Aldehydes and ketones

  • 1. CHEMICAL PROPERTIES OF ALDEHYDES AND KETONES By:Takeen Khurshid To: Dr. Geeta Durga
  • 2. Aldehydes: General formula: RCHO or RCH=O Ketones: General formula: RCOR’ (R and R’=alkyl or aryl)
  • 3. Naming Of Aldehyde: •Select the longest continuous carbon chain that contains the C=O group and replace the ending by the suffix al. •The CHO group is assigned the number 1 position and takes precedence over other functional groups that may the present such as –OH, C=C.
  • 4. Common name: listing the alkyl substituents attached to the carbonyl group, followed by the word ketone. IUPAC system: replace the ending –e by the suffix –one. The chain is numbered in such a way as give the lowest number to the C=O group. Common Dimethyl ketone Methyl phenyl ketone Methyl vinyl ketone Diphenyl ketone Acetone Acetophenone Benzophenone IUPAC Propanone Phenyl ethanone 3-Buten-2-one Diphenylmethanone CH3 C CH3 O CH3 C C6H5 O CH3 C CH=CH2 O H5C6 C O C6H5 Naming Of Ketone
  • 5.  Because the polarity of the carbonyl group, aldehydes and ketones are polar compounds.  Dipole-dipole attractions, although important, are not as strong as interactions due to hydrogen bonding. As a result, the boiling points of aldehydes and ketones are higher than those of nonpolar alkanes, but lower than those of alcohols.  The lower aldehydes and ketones are soluble. C O C + O - O C O C δ − δ − δ + δ + C O H O H CO δ − δ + δ + δ −
  • 6. C+δ O-δ H H C+δ O-δ H R C+δ O-δ R' R > > Activity of the carbonyl group C+δ O-δNu- C O-Nu E+ C OENu
  • 8. Aldehydes & ketones, reactions: 1) Oxidation 2) Reduction 3) Addition of cyanide 4) Addition of derivatives of ammonia 5) Addition of alcohols 6) Condensation Reactions 7) Addition of Grignard reagents 8) (Alpha-halogenation of ketones) 9) Cannizzaro reaction
  • 9. Aldehydes and ketones Alcohols Lactones and esters Oximes Amides CyanohydrinsEnols and enolate anions Hydrazones Alkenes Alkanes Ketals and thioketals Carboxyllic acids
  • 11. 1- Reduction of carbonyl group a- Addition of metal hydride CH3 O H 2 H2 / Pd CH3 OH CH3 OH 1) NaBH4 2) H2O C O C O-M+H C OHH+ M+ H- H2O H+ H2O H+ O LiAlH4 OAl H OH
  • 12. R C O H R CH OH R' R C OH R' R'' R C R' O + R'MgX 1) Dry ether 2) H2O + R''MgX 1) Dry ether 2) H2O CH3 C O H CH3 CH OH C2H5+ C2H5MgX 1) Dry ether 2) H2O + CH3MgX 1) Dry ether 2) H2O O CH3 OH b- Addition of Grignard Reagents: Formation of alcohols
  • 13. c- Clemmenson reduction d- The Wolf-kishner reduction O COOH HCl / Zn(Hg) COOH H H COOH O NH2NH2 COOH N-NH2 COOH NaOH ∆ H H
  • 14. e- Wittig reaction C O + CH2=P(C6H5)3 THF C O- CH2 P(C6H5)3 C O CH2 P(C6H5)3 C CH2 + (C6H5)3P=O H O + (Ph)3P=CH C OC2H5 O OC2H5 O
  • 15. 2- Oxidation reaction a- b- Tollenis test c- Iodoform reaction R-CHO or Ar-CHO KMnO4 or K2Cr2O7 RCOOH or ArCOOH RCOO- + 2 Ag(NH3)+ 2 + OH- + 2 Ag + 4 NH3 + 3 H2ORCHO C O CH3 R + 3 I2 + 4 NaOH R O O - Na + + CHI3 + 3 NaI CH3 CH3 O I2 / NaOH CH3 COONa + CHI3
  • 16. R C OH R' CN R C R' O + HCN O H + HCN OH CN Cyanohydrin Benzaldehyde cyanohydrin O + HCN OH CN H2 / Pt or LiAlH4 and H3O + OH NH2 H3O + Heat OH COOH 3- Addition of Hydrogen Cyanide: Formation of cynohydrins
  • 17. R C O R 2 R C OH R'O R 2 + R'OH CH3 C O H CH3 CH OH OC2H5 + C2H5OH H + R''OH H + R C OR'' R'O R 2 R 2 =H: R 2 =Alkyl Aldehyde Ketone Hemiacetal Hemiketal Acetal Ketal H + C2H5OH H + CH3 CH H5C2O OC2H5 Hemiacetal Acetal CH3 C O CH3 CH3 C OH OC2H5 CH3 + C2H5OH H + C2H5OH H + CH3 C H5C2O OC2H5 CH3 Hemiketal Ketal 4- Addition of alcohols:
  • 18. C O NH3 C NH Imine NH2OH Hydroxylamine C N OH C N NH2 C N NH C N NH O2N NO2 C N NH C NH2 O Oxime NH2 NH2 Hydrazine Hydrazone NH2 NH Phenylhydrazone Phenylhydrazine NH2 NH O2N NO2 2,4 - Dinitrophenylhydrazone NH2 NH C NH2 O Semicarbazide Semicarbazone 6- Addition of Ammonia and Ammonia Derivatives
  • 19. 7.ALDOL CONDENSATION  Condensation between two molecules of an Aldehyde or a ketone to form a β-hydroxyl aldehyde or a β-hydroxy ketone is known as a ALDOL CONDENSATION.  ALDOL CONDENSATION is possible only when the carbonyl compound contains atleast one α-hydrogen atom.
  • 20. MECHANISM enolate ion An enolate ion is the anion formed when an alpha hydrogen in the molecule of an aldehyde or a ketone is removed as a hydrogen ion.
  • 21. The alkoxide ion is the conjugate base of alcohols.
  • 22. Alkoxide ion is protonated by water.
  • 23. Crossed aldol condensation In the presence of a strong base, two different molecules of aldehyde or ketone combine to form a β-hydroxyaldehyde or a β-hydroxyketone. This reaction is called as the aldol condensation.
  • 24. The enolate ion (carbanion) is the actual nucleophilic reagent. The reaction breaks down to the following: The α-carbon of the donor attaches itself to the carbonyl carbon of the acceptor.
  • 25. Step 1: Deprotonation and formation of nucleophile. • Step 2: Attack by nucleophile: Formation of alkoxide ion.
  • 26.  Step 3: Hydrolysis and formation of Aldol type product Step 4: Intramolecular dehydration
  • 27. 8- Cannizzaro reaction Aldehyde which does not contain α hydrogen undergoes Cannizzaro reaction. CHO + NaOH (30 %) ∆ + CH2OH COO- Na+ CH + OH- C O- OH O H C C CH2O- + OH O O H C CH2OH + O- O more stable anion