1. Ch 13 Carboxylic Acids, Esters, Amines and Amides SWBAT: Name/Draw compounds with functional groups Describe/Explain properties of functional groups Complete/Show reactions of functional groups

2. Chapter 13.4 Amines

3. Amines They are derivatives of ammonia NH 3 H-groups are replaced by alkyl or aromatic groups

4. Subclasses of Amines

5. Naming Amines Similar to ether… List the alkyl groups in alpha order No gaps Ends in -amine methylamine dimethylamine

6. Practice ethylmethylpropylamine ethyldimethylamine triphenylamine

7. Aromatic Amines Aromatic amines use the name aniline Amino bearing Carbon is C#1 2,6-diethyl-4-methylaniline aniline

8. Naming Anilines N-ethylaniline Alkyl groups attached to the nitrogen of the aniline are named with the prefix N- followed by the alkyl name N, N-dimethylaniline

9. Properties of Amines Boiling Point Amines can have polar N-H bond, so they can form H-bonds But…N is not as electronegative as the O in alcohols…so the H-bonds are weaker! BP is below Alcohol Bp differences among different types of amines! 1 o amines highest BP (2 H-bonds) 2 o amine lower (1 H-bond) 3 o amine lowest (only dipole)

10. Properties of Amines Solubility Amine group is polar: soluble in water, will form H-bonds Small amines (1-5 C atoms) are soluble Large amines (<6 C atoms) are not

11. Famous Amines Acetyl choline – neurotransmitter Nicotine

12. Famous Amines Prozac – Fluoxetine Caffeine

13. Reaction of Amines A.1 o and 2 o Amines react as Bases – they accept H + ions like ammonia below: The unpaired valence e- of N attract H+ H + H-N-H + H 2 O → H-N-H + OH - H H NH 3 + H 2 O → NH 4 + + OH - ammonia ammonium ion

14. Reacting as a Base Primary Secondary Tertiary amines do not react! dimethyammonium ion Dimethylamine

15. Neutralization Reaction Base + Acid → Salt NH 3 + HCl → NH 4 + Cl - Ammonia Ammonium chloride (salt) a) Primary amine CH 3 -NH 2 + HCl → CH 3 -NH 3 + Cl - Methylamine methylammonium chloride b) Similar for secondary amine

16. Homework Chapter 13 Page 448 13.34 – 13.44 (even)