Organic Chem Class # 5

1. Organic Chem Class # 5 My Aunt Ester Acids, esters, amine and amides Made easy and palatable by yours truly. Peace Love + Organic Chem

2. An organic acid will release H+1 ions, but has a different look than our “regular” acids. The only acid in table K that is organic is ethanoic. Ethanoic acid has a different sort of formula as well. All organic acids have a “—COOH” group. It’s that last H that will ionize away. • O • C—OH O R—C R • OH Computers make this easier to type. Both are ok. We’ll draw it this way most of the time.

3. Draw Methanonic Acid Ethanonic Acid Propanoic Acid And Hexanoic Acid

4. O H—C—OH H—C—C—OH H—C—C—C—OH Draw Methanonic Acid Ethanonic Acid Propanoic Acid And Hexanoic Acid H O H H O H H H H H HHH O C C C C C C H H H HHHH

5. When you combine an organic acid with an alcohol you will end up with an ester and water. This is called ESTERFICATION. One of the best smells ever is the ester in bananas!

6. The functional group for esters is: O R —C—O—R’ On one side there’s an R group. On the other side there’s a different one.

7. Unlike a lot of molecules, such as the ethers, or even most of the halocarbons, these molecules are not just left and right. There are 2 parts. To help you remember (me too) I call one side the “oxygen tail”. That’s the part that gets named first. Let’s look at the reference table at methyl propanoate. (the methyl = 1, the prop = 3) -anoate is the suffix to the name. O CH3CH2-C-O-CH3 The “propanoate” is on this side, it counts the 3 carbons on the left. The “methyl” is on this side, AFTER the oxygen atom.

8. To draw an ester, start with the functional group and work out from there. Draw butyl pentanoate. O ―C―O― The “oxygen tail” side get the first part of the name (butyl). The “other” side gets the last part of the name (penta), and it INLCUDES that carbon in the functional group.

9. Do the oxygen tail side first, the butyl side Draw butylpentanoate. O ―C―C―C―C―C―O―C―C―C―C―

10. We will ALWAYS name the “R” group on the oxygen tail FIRST. The R groups will be Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonly, or decyl. There are no other choices. On the “other” side of the ester, we’ll start with table P names, but they end in –anoate, like: Methanoate, ethanoate, propanoate… or octanoate, nonanoate, or decanoate. Draw these now… Methyl hexanoate Propyl ethanoate Ethyl propanoate Ethyl methanoate

11. Methyl Hexanoate Ethyl methanoate Propyl ethanoate Ethyl propanoate

12. Draw one more, get it right the first time. No mistakes… Propyl propanoate

13. This man does not play baseball for New York Yankees. Why is he here?

14. Propyl propanoate

15. Amines and Amides are similar (in the same way the aldehydes and ketones were). The Amines and Amides are both NITROGEN containing compounds. Amines are in the middle of a chain, where amides are on the end of a chain. Location, location, location! Count to 3 for nitrogens, they always make 3 bonds.

16. AMINES • AMIDES R’ R―N―R” O H R―C―N―H The nitrogen atom is in the center of three “R” groups. In college organic chem, these would be three hydrocarbon chains of any length. In our class, the R’ and R” groups will always be hydrogen atoms.. Amines can be attached to any carbon in a chain. Amines for us will be R―NH2 These groups are always at the end of a chain, and the nitrogen is attached to a carbon which is also attached to an oxgyen. Although the “N” could have 2 chains, it will only have 2 hydrogen atoms in our class. Amides for us will be O H R―C―N―H

17. Draw 4-octanamine and hexanimide

18. 4-octanamine • hexanimide C C C C C C C C N―H H O C C C C C C N―H H

19. I will collect on Thursday Organic chem Homework #2 It’s 3 pages of molecules. No mistakes, use your reference tables. Check out the 100 Questions!