1. Organic Chemistry Functional Groups: - Aldehydes - Ketones
- Organic Acids
- Esters
- Amines
- Amides

3. Aldehydes
Group is always on a terminal C – no need to specify location by number
Condensed it is symbolized by a -CHO group at the end of the formula
C = O is known as a carbonyl group
Drives the physical and chemical properties of these compounds
Aldehydes have characteristic scents and tastes
Cinnamon is an example

4. Aldehydes
Drop the –e from the end of the alkane and add –al; C=O is C #1
Name these two compounds:
Methanal
(formaldehyde)
Butanal

5. Ketones
Like the aldehydes the Functional group is the carbonyl group C=O
Contains an alkyl group on either side of the C=O
In aldehydes one side is an alkyl group the other is H
Often used as a solvent
Acetone is one example

6. Naming Ketones Number the C chain so C=O has the lowest #
Drop the final e from the alkane name and add -one
Name these compounds:
4-methyl-2-pentanone
C-C-C-C-C C o
3-hexanone

7. Properties Both aldehydes & ketones have A carbonyl functional group.
C=O is polar & their compounds
Are polar. This leads to:
Higher B.P’s than non-polar molecules
Lower than alcohols that can
H-bond w/ each other
Can not H-bond between each other
but can H-bond to solvents like water
- Lower MW compounds
are appreciably soluble in water
Propanone Propanal

8. Properties Butane Diethyl ether Propanal Propanone 1-propanol M.W. 5860
B.P (deg.C) 35 49 56 97
Solubility
g/100g H2O
Insol. 8 16
Fully
miscible
Fully miscible

9. Organic Acids Condensed form is written –COOH
A carbonyl group and a hydroxyl group bonded to C
Known as a carboxyl group
A terminal functional group
The carboxyl group is an organic acid.
It is the H on the end of COOH that is donated as a proton (H+)
What is left is the anion R-COO-

10. Carboxylic acids ionize in water to form a proton and
A carboxylate anion

11. Naming Organic Acids The carboxyl group is a terminal group
no need to give it a number. It’s always on C #1
Drop the –e from the alkane name and add –oic acid
Name this compound:
Butanoic acid

12. Naming Organic Acids Name this compound: Name this compound:
Butanoic acid
Name this compound:
2,4-dimethylhexanoic acid
C-C-C-C-C-COOH
C C

13. Some Common Carboxylic acids
CH3C=O OH
HC=O OH
Ethanoic Acid
“Acetic Acid”
Methanoic acid
“formic acid”
The sting of ants
Vinegar
C-C-C-COOH
Butanoic acid
Rancid butter smell

14. Physical properties Sharp or noxious smells
polar and can form 2 hydrogen bonds with themselves and with water
C-C=O OH HO
O=C- C
C-C=O OH H O
This leads to high B.P. and high solubility in water
- 1st four acids are totally miscible in water

15. Comparison of properties
Butane
Diethyl
ether
Propanal
Propanone
1-propanol
ethanoic
M.W. 58 60
B.P (deg.C) 35 49 56 97
118
Solubility
g/100g H2O
Insol. 8 16
Fully
miscible
Fully miscible

16. Esters Esters are derivatives of Carboxylic acids
Combination of an Alcohol and an Acid
The alcohol provides the alkyl portion of the ester name
Esters are polar but can not form hydrogen bonds with one another
BP’s of esters are lower than alcohols or acids with similar mass

17. Physical properties M.W. 72 74 B.P (deg.C) 76 80 57.5 118 141 Butanal
Butanone
Methyl ethanoate
1-butanol
Propanoic
Acid
M.W. 72 74
B.P (deg.C) 76 80
57.5
118
141

18. Properties Esters have distinctive odors (flowers, flavors etc.)
- Function of which alcohol is combined with which acid
Alcohol
Acid
Ester
Fragrance
Ethanol
Butanoic acid
Ethyl butanoate
Pineapple
Pentanol
Ethanoic acid
Pentyl ethanoate
Banana
Octanol
Octyl ethanoate
Orange
Methanol
Salicylic acid
Methyl salicylate
wintergreen
Methyl butanoate
apple

19. Naming Esters
Esters are not a terminal group but they are unique because of the carboxyl group therefore the carbonyl carbon is considered to be C #1
Name the group attached to the hydroxyl oxygen first (the alkyl group)
Next name the carboxylate carbon chain, dropping the –e and adding –oate
Written condensed format is RCOOR’

20. Name this compound:
Ethyl butanoate
Name this compound: O
CH3-C-O-CH2-CH2-CH-CH3
CH3
3-methylbutyl ethanoate

21. What alcohols and acids produce the above esters?
(Not IUPAC)
2-methylbutyl ethanoate
What alcohols and acids produce the above esters?

22. (Not IUPAC)

23. Amide
Like esters the amide functional group is a derivative of carboxylic acids
OH replaced by the amine group
The amide group is a terminal group
Important biological molecules
Links amino acids together to form proteins

24. Amide Physical Properties
Amides have very high BP’s due to strong
intermolecular hydrogen bonding
- higher than similar esters and acids
- H-bonding can occur between N, H and O
CH3 – C=O
NH2
CH3COOCH3
CH3COOH
CH3COONH2
B.P. (deg. C)
57.5
118
221

25. Amide
Take the name of the alkane with the same number of carbon atoms
Drop the –e from the alkane name and add –amide
Amide carbon is carbon #1 when naming side chaines
Ethanamide

26. Name this compound:
C-C-C=O
C NH2
2-methylpropanamide

27. Amines Nitrogen is the functional part of an amine
Nitrogen can form three bonds (just like NH3)
One must be to the carbon chain
The other two bonds can be to Carbon and/or H2
C-C-NH2 or
Primary
Amine
C-C-N-H or C
Secondary
Amine
C-C-N-C C
Tertiary
Amine

28. Physical properties of Amines
Like ammonia, amines are polar compounds
H can also be Carbon
Based groups
And like ammonia, amines are Bronsted-Lowery
Bases
- both are Proton acceptors H
:N-H H+

29. Physical properties of Amines
- Since amines can act as proton acceptors reaction
With a proton donor like HCl will lead to a salt,
i.e. an ionic compound H
:N-H H
:N-H
HCl +
Cl- H

30. Physical Properties of Amines
Amines can hydrogen bond like alcohols or
Carboxylic acids
- Contains N and H
- H-bonding raises the B.P. but it is not as high as the alcohols or acids H
C-C-N
Ethanoic acid
Ethanol
Ethyl amine
B.P. (deg C)
118 78 17 H
N-C-C
Tertiary amines have higher BP’s than secondary and secondary is higher than primary

32. Physical properties of Amines
Amines can H-bond with water
Leads to high water solubility up to about 6C
Methyl
Amine
Ethyl
Propyl
Butyl
Sol
(g/100g H20)
v. Sol
Totally
miscible
Miscible
v. sol
Amines have very strong odors
Methyl and ethyl amine smells like ammonia
Higher MW amines often have a fishy smell
Aromatic amines are generally toxic
Readily absorbed through skin often with fatal results

34. Amines Need #’s to designate the location of the amine
Name your carbon chain as an alkane, drop the –e and add –amine
If there are 2 amines indicate their location and add –diamine to the alkane name
2-butanamine

35. Name this compound:
C-C-C-C-C-C
N N
1,3-hexadiamine

36. Amino Acids Related to amines are the Amino Acids
If you have a “N” and a COOH it is an amino acid
GLYCINE
Since the amino group is a proton acceptor and the
Carboxylic acid is a proton donor amino acids are
Actually NH3+ and COO-.