CH2210 Aldehydes and Ketones
Alcohols Phenols Ethers Thiols Dissulfides Amines
-O- -S- -N-
OC
Alkanes Alkenes Alkynes Aromatics
Aldehydes Ketones Acids Esters Anhydrides Amides
OC-N
OC-O
Hydrocarbons
All Classes of Organic Compounds
Functionalized Hydrocarbons
Halides
F,Cl,Br O,S,N
OC
C O:
:
! bond
Structure of the Carbonyl Group
The carbonyl group is constructed in the same manner as the carbon-carbon double
bond, from an sp2 hybridized carbon atom and an sp2 hybridized oxygen atom.
4 electrons
C O:
:π bond
! bond
:
Structure of the Carbonyl Group
The carbonyl group is constructed in the same manner as the carbon-carbon double
bond, from an sp2 hybridized carbon atom and an sp2 hybridized oxygen atom.
.
.
Structure of the Carbonyl Group
C O
The angles between the three bonds to carbon
involved are approximately 120º.
Families Containing the Carbonyl Group
O
CZY
Family Y Zaldehyde H or C H
ketone C Ccarboxylic acid H or C -O-H
ester H or C -O-Camide H or C -N
Common Aldehydes and Ketones
CH2OFormaldehyde
Names for Simple Aldehydes and Ketones
CO
H H
CO
CH3 H
CO
CH3CH2 H
CO
CH3CH2CH2 H
CO
CH3 CH3
Compound Common name
Systematic name
formaldehyde methanal
acetaldehyde ethanal
propionaldehyde propanal
butyraldehyde butanal
acetone (dimethyl ketone) propanone
CO H
Benzaldehyde
Another Common Aldehyde
Names for More Complex Compounds
CO
CH2CH2CH HCl CH3
CH3CH2CCHCHCH3CH3
Br
O
4-chloro-2-methylbutanal
3-methyl-2-butanone 4-bromo-5-methyl-3-hexanone(isopropyl methyl ketone)
CO
CH3 CHCH3
CH3
CO
CH3 CHCH3
CH31
234
2
1 3
4
31 2
4
5 6
Additional Nomenclature Examples
CH2CH2
CH2C
O
CH3O
CH3
CH O
NO2
5-phenyl-2-pentanone 2-methylcyclopentanone
3-nitrobenzaldehyde (meta-nitrobenzaldehyde)
1
2
13
4
5
1
2
Physical Properties of Aldehydes and KetonesSummary of Important “Secondary Forces”
Which Contribute to boiling Points
Seco
ndar
y A
ttra
ctiv
e Fo
rces
London
Dipole-dipole
H-bonding
Increased Boiling Point
Hydrocarbons
Aldehydes and Ketones
Alcohols
Amines
240
200
160
120
80
40
-
-
-
-
-
-
Boili
ng P
oint
Physical Properties of Aldehydes and Ketones
I I I I I 40 80 120 160 200 Molecular Mass
Alcoho
ls
Alde
hyde
sAlkan
es
Physical Properties of Aldehydes and Ketones Water Solubility
CO
H H
CO
CH3 H
CO
CH3CH2 H
CO
CH3CH2CH2 H
CH3CH2CH2CH2CO
H
Compound Boiling Point (ºC) Water solubility (g/100 mL H2O)
-21 very soluble
21 very soluble
49 16
76 7
103 1
Physical Properties of Aldehydes
Physical Properties of Ketones
H3CC
CH3
O
CCH3
O
CH3CH2
CCH3
O
CH3CH2CH2
CCH3
O
CH3CH2CH2CH2
CCH3
O
CH3CH2CH2CH2CH2
Compound Boiling Point (ºC) Water solubility (g/100 mL H2O)
56 very soluble
80 26
102 6
127 -
151 -