The Carbonyl Functional Groups
Chapter 14, 15, 16
Suggested Problems:
Chapter 14: 3-12
Chapter 15: 5-8

O
C
The Carbonyl Group
• A C=O group is called a carbonyl group
• Depending on what else is bonded to the carbonyl carbon, we have aldehydes, ketones, carboxylic acids, esters and amides

Aldehydes
• The functional group of an aldehyde is a terminal carbonyl group (there is a hydrogen on the carbonyl carbon)
• The generic formula of an aldehyde is
R
O
C H

Examples: Aldehydes
• An example of an aldehyde is acetaldehyde
O
C
CH
3
H ethanal acetaldehyde

Naming Aldehydes
• The suffix for aldehydes is “al”
H
O
C H
O
CH
3
CH
2
CH
2
C H

Ketones
• The functional group of a ketone is an internal carbonyl group (the carbonyl carbon is bonded to two alkyl groups)
• The generic formula of a ketone is shown below
• R and R’ may be the same alkyl groups, or they may be different
O
R C R'

Naming Ketones
• Acetone is the simplest ketone
• The suffix for ketones is “one”
O
C
CH
3 propanone acetone
CH
3

Carboxylic Acids
• The functional group of carboxylic acid is the carboxyl group
–Carboxyl = carbonyl + hydroxyl
R
O
C OH

Naming Carboxylic Acids
• The suffix for carboxylic acids is “oic acid”
• An example of a carboxylic acid is acetic acid
O
C
CH
3
OH ethanoic acid acetic acid

Example
O
CH
3
CH
2
CH
2
C OH

Esters
• The generic formula of an ester is:
O
R C OR'
• Esters are condensation products between carboxylic acids and alcohols
O
R C OH H O R
O
R C O R

An Example of an Ester
• An example of an ester is pentyl acetate, an artificial banana flavor
CH
3
CH
2
CH
2
CH
2
CH
2
O
O C CH
3 pentyl ethanoate pentyl acetate

O
O C
Examples of Esters
CH
3
C OH
O acetyl salicylic acid
(aspirin)
OH
C O
O
CH
3 methyl salicylate
(wintergreen)

Amides
• The generic formula of an amide is:
R
1
O
C N
R
3
R
2
• Amides are condensation products between carboxylic acids and amines
O
R C OH H NR
2
O
R C NR
2

An Example of an Amide
• An example of an amide is acetaminophen, an analgesic
O
CH
3
C
N
H acetaminophen
Tylenol
®
OH

Alkane
C-C single bond
Aldehyde
Terminal carbonyl (C=O), RCHO
Alkene
C=C double bond
Alkyne
C ≡C triple bond
Aromatic
Benzene ring
Ketone
Carbonyl (C=O), R
2
C=O
Carboxylic Acid
Carboxyl group, RCO
2
H
Ester
Carboxylic acid + alcohol, RCO
2
R’
Alcohol
Hydroxyl group, ROH
Amide
Carboxylic acid + amine, RCONR
2
Ether
Oxygen bridge, ROR’
Amine
Nitrogen, R
3
N
No Naming of Amides and Esters

Identify the Functional Groups
HO
Ethynylestradiol
“novestrol”
Ortho-Cyclen
OH
C CH

Identify the Functional Groups
CH
3
N
O
C OCH
3
O
O C
This is cocaine

Identify the Functional Groups
CH
2
O
C
H H
N
O
H
N
S
CH
3
CH
3
C OH
O
Penicillin G

Identify the Functional Groups
HO CH
3
OH
H
N(CH
3
)
2
OH
What is the total number of functional groups?
OH O OH
OH
O
Oxytetracycline antibiotic
CONH
2