Naming: linear backbone
O
O
OH
propane
propanoic acid
O
propanoic anhydride
O
O
O
O
Cl
H
propanal
propanoyl chloride
O
O
NH2
propanamide
N
O
propanone
methyl propanoate
propanenitrile
1
Naming: attached to a ring
O
Cl
cyclohexanecarbonyl chloride
cyclohexane
O
O
OH
NH2
cyclohexanecarboxylic acid
cyclohexanecarboxamide
O
N
O
methyl cyclohexanecarboxylate
cyclohexanecarbonitrile
Naming: attached to a (benzene) ring
O
Cl
benzene
benzenecarbonyl chloride
benzoyl chloride
O
O
OH
NH2
benzenecarboxylic acid
benzoic acid
benzenecarboxamide
benzamide
O
N
O
methyl benzenecarboxylate
methyl benzoate
benzenecarbonitrile
benzonitrile
3
Numbering the position of a substituent:
Naming carboxylic acids
Acyl halides:
Acid anhydrides:
Esters:
8
Lactones (cyclic esters):
butano-4-lactone
2-oxacyclopentanone
pentano-5-lactone
2-oxacyclohexanone
hexano-5-lactone
3-methyl-2-oxacyclohexanone
9
Amides:
 Caution: be aware of the difference between
10
amides and amines.
How to name a lactam (cyclic amide)?
butano-4-lactam
propano-3-lactam
2-azacyclopentanone
2-azacyclobutanone
11
Some examples:
?
?
O
O
?
O
Cl
ethyl 2-chloro-3-methoxypentanoate
12
Some examples:
O
O
O
Cl
ethyl 2-chloro-3-methoxypentanoate
13
 Important common names:
formic acid
acetic acid
dimethylformamide
acetyl chloride
acetic
ti anhydride
h d id
ethyl acetate
acetonitrile
14
Structure of carbonyl compounds:
15
Resonance:
16
Intermolecular interactions:
Hydrogen bonds > dipole-dipole > van der Waals forces
17
Relative boiling points:
amide > carboxylic
y acid > nitrile >> ester, acyl
y chloride,
aldehyde, ketone
18