1. Chapter Fifteen
Amines

2. Goals Recognize primary, secondary, tertiary, and heterocyclic amines
Recognize quaternary ammonium ions.
2.   Name simple amines & write their structures,
 Describe amines in terms of hydrogen bonding, solubility, boiling point, and basic nature
4.   Be able to predict the products of the acid–base reactions of amines and ammonium ions.
5.  Describe properties of typical of amines.

3. Amines
A compound that has one or more organic groups bonded to nitrogen:

4. The importance of the NH4+ ion
Each amine N atom has a lone pair of electrons.
This lone pair is responsible in large part for the chemistry of amines.
When a fourth group bonds to the nitrogen through this lone pair a quaternary ammonium ion, which has a permanent positive charge and forms ionic compounds with anions.

5. Amines are Basic Amines exist as ammonium ions in blood and other
body fluids  resulting in high pH.
aromatic amine ammonia non-aromatic amines
Aqueous solutions of amines are basic because of the formation of Ammonium ions. Positive ions formed by addition of H+ to ammonia or an amine.
Nonaromatic amines are slightly stronger bases than ammonia, which is stronger than aromatic amines.
Amines exist as ammonium ions in the aqueous environment of blood and other body fluids.
Strength of the base

6. Amines are Basic
Because of the basic nature, they are often referred to as Alkaloids
Man has a long history of extracting amines from plants for medicinal and recreational uses
Codein: A heterocyclic amine

7. Protein contains amine groups
Volatile amines produced during decay are responsible for the odor of rotten fish or decaying meat.
Cadaver-sniffing dogs are used to detect the strong odor of the amines produced from decaying flesh.
Some complex amines from plants can be very poisonous. Many useful drugs are amines.

8. Pharmaceutical Amines
Diphenhydramine is an over-the-counter antihistamine.
Antihistamines of this type are oily liquid, and are converted to amine salts to be used formulated for use as medicine
Diphenhydrammonium chloride is also called Diphenhydramine hydrochloride

9. Naming Primary Amines Identify the alkyl group attached to nitrogen
Add the suffix -amine to the alkyl group name

10. Secondary and Tertiary Amine
Named by adding di- or tri-, to the alkyl group name along with the suffix -amine.
Dipropylamine
Triethylamine

11. Classify the amine shown below as primary, secondary, tertiary, or quaternary.
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12. Complex 2o and 3o Amines  we call it N-Ethylpropylamine
The parent compound is chosen as the 1 amine that contains the largest of the R groups.
All other groups are are treated as N-substitute groups
The largest chain is propane thus the compound is a propylamine
2. It has a ethyl R group :
 we call it N-Ethylpropylamine

13. Name the amine shown below.
N-ethyl, N-methylpropylamine
N-ethyl, N-propylmethylamine
N-methyl, N-pentylamine
N-methyl, N-propylethylamine
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14. Who am I? N-ethyl-N-methyl-N-hexyl amine N-methyl-N-ethyl hexylamine
N-hexyl-N-methyl ethyl amine  
N-ethyl-N-methylhexyl amine

15. Who am I? N-ethyl-N-methyl-N-hexyl amine N-methyl-N-ethyl hexylamine
N-hexyl-N-methyl ethyl amine  
N-ethyl-N-methylhexyl amine

16. Aromatic Amine’s
The simplest aromatic amine is known by the common name aniline.
The methy group is treated as a substitution onto the Aniline

17. Amino Group –NH2 is also a functional group (amino group)
when this group is treated as a substituent amino- is used as a prefix.
3-Aminopropanoic acid

18. Properties of Amines
The lone electron pair on the N in amines causes amines to be weak bases: . .
Electron pair donors that form a bond with H+ in water

19. Physical Properties
Because of hydrogen bonding, 1 and 2 amines have higher boiling points than alkanes of similar size.
Amines have less hydrogen bonding, and lower boiling than alcohols of similar size.
All amines can hydrogen-bond to water molecules through the lone electron pair on their nitrogen atoms.
Amines with up to about 6 C’s are soluble in water.

20. 3 amine molecules have no H atoms attached to N and therefore cannot hydrogen-bond with each other. As a result they are much lower boiling than alcohols or 1 or 2 amines of similar molecular weight.

21. Heterocyclic Nitrogen Compounds
Heterocycle: A ring that contains nitrogen or some other atom in addition to carbon in the ring structure
Heterocycles are common in many natural compounds found in plants and animals.

22. Heterocyclic Nitrogen compounds

23. Heterocyclic Nitrogen compounds
Look for # of nitrogen atoms and # of carbon atoms
This compound has 2 nitrogen atoms and 4 carbon atoms

24. Heterocyclic Nitrogen compounds
Look for # of nitrogen atoms and # of carbon atoms
This compound has 4 nitrogen atoms, and 5 carbon atoms

25. Basic Nature of Amines
Amines exist as ammonium ions in the aqueous environment of blood and other body fluids, which typically have a pH value of 7.2
When you see amine compounds represented – they are normally shown as ions.

26. Amines are Basic Amines exist as ammonium ions in blood and other
body fluids  resulting in high pH.
aromatic amine ammonia non-aromatic amines
Aqueous solutions of amines are basic because of the formation of Ammonium ions. Positive ions formed by addition of H+ to ammonia or an amine.
Nonaromatic amines are slightly stronger bases than ammonia, which is stronger than aromatic amines.
Amines exist as ammonium ions in the aqueous environment of blood and other body fluids.
Strength of the base

27. Naming Amine ions
The positive ions formed by addition of H+ to alkylamines are named by replacing the ending –amine
by -ammonium.
To name the ions of heterocyclic amines, the amine name is modified by replacing the -e with -ium.

28. Amine Salts Composed of an ammonium cation and an anion
Ammonium salts are generally odorless, white, crystalline solids that are much more water-soluble than neutral amines because they are ionic.

29. Quaternary ammonium ions
Permant + charge  structures in solution that are are unaffected by changes in pH.
Benzalkonium chlorides, used in surgical scrubs and storage of surgical instruments have both antimicrobial and detergent properties.

30. Amines in Plants: Alkaloids
Naturally occurring, nitrogen-containing compound isolated from a plant
Usually basic, bitter, and poisonous
The bitterness and poisonous nature of alkaloids probably evolved to protect plants from being devoured by animals.

31. Physiologically Active Alkaloids
Caffeine and nicotine are stimulants.
Others are notable as pain relievers (analgesics), as sleep inducers, and for the euphoric states they can create.