1. Goals of the Day… Briefly review naming (from the online lesson)
Please turn in your worksheet)
Look at the physical properties of carboxylic acids and esters. 

2. Write the name of the acid in your notebook…

3. Answer…7-fluoro octanoic acid…
(remember that the acid carbon is always carbon #1, so the groups on the chain have to get the “corresponding number” …

4. Write the name of the ester below in your notebook…
There is a hint on the next slide. 

5. Remember that the esters are named in 2 sections…
First name the group on the oxygen.
Then name the rest of the chain.

6. Remember that the esters are named in 2 sections…
First name the group on the oxygen.
Then name the rest of the chain.

7. Ethyl hexanoate First name the group on the oxygen: ethyl.
Then name the rest of the chain, there are 6 carbons, so it is hex…anoate.

9. Physical Properties for… Carboxylic Acids
M.P./ B.P. rankings
Water Solubility
Acidity
Rankings are…
Groups with hydrogen bonding
Groups with dipoles
Groups with van der Waals forces

10. Polarity of Carboxylic Acids
are strongly polar.
have two polar groups.
hydroxyl (−OH) and carbonyl (C═O)

11. Boiling Points of Carboxylic Acids
The boiling points (bp) of carboxylic acids
are higher than those of alcohols, ketones, and aldehydes of similar mass.
are high because they form dimers in which hydrogen bonds form between two polar carboxyl groups.

12. Comparison of Boiling Points

13. Melting Point/ Boiling Point Ranks
Rank these in order of their melting point temperatures (high to low)…
> > > > _____

14. Melting Point/ Boiling Point Ranks
Rank these in order of their melting point temperatures (high to low)…
a c e d b
> > > > _____

15. Solubility in Water Carboxylic acids
form hydrogen bonds with many water molecules.
with 1 to 4 carbon atoms are very soluble in water.
Water molecules

16. Boiling Points and Solubility
Solubility in Water (continued on the following slide..>
Boiling Points and Solubility

17. Boiling Points and Solubility

18. Water Solubility…
Which would be soluble in water?

19. Water Solubility Answer…
Just the alcohol (a)
The ether (b) is basically not soluble (slightly soluble)
C is an alkane
D has too many carbons

20. Acidity of Carboxylic Acids
are weak acids.
ionize in water to produce carboxylate ions and hydronium ions.

21. Acid Dissociation Constants
Carboxylic acids
have small acid dissociation constants.
exist mostly as molecules and a few ions in aqueous solutions.

22. Neutralization of Carboxylic Acids
Carboxylic acid salts
are a product of the neutralization of a carboxylic acid with a strong base.
are used as preservatives and flavor enhancers.

23. Boiling Points of Esters
The boiling points of esters
are higher than for alkanes of similar mass.
are lower than alcohols and carboxylic acids of similar mass because esters cannot form hydrogen bonds with each other.

24. Melting Point/ Boiling Point Ranks
Rank these in order of their melting point temperatures (high to low)…
> > > > _____

25. Melting Point/ Boiling Point Ranks
Rank these in order of their melting point temperatures (high to low)…
c e b a d
> > > > _____

26. Solubility in Water Esters
are soluble in water when they have 1–5 carbon atoms.
form hydrogen bonds from the partial negatively charged carbonyl oxygen to the partial positively charged hydrogen atoms in water.
decrease their solubility in water with an increase in the number of carbon atoms.

27. Which are soluble in water?

28. Which are soluble in water?
All but the last one, propane, are soluble in water! 

29. Reactions… Some you already know (so just review)
Removing a proton (using a base)
Forming an ester!  (oh, so sweet! ). 

30. Reactions that you know to make carboxylic acids….
Oxidation of primary alcohols or aldehydes
Reagents can be H2CrO4, CrO3, [O], PCC, Benedicts, etc.
Primary alcohols & aldehydes can be oxidized to carboxylic acids

31. Removing a hydrogen! (remember, they are acids!) 

32. The main Carboxylic Acid Reaction (need to be acid or base catalyzed)…
Esterification… Important in fats
Note 1: this is why esters are named the way they are…because they come from
Carboxylic acids! 
Note 2: This is an equilibrium reaction – this means it can also go “backwards.”

33. Esterificaton & Hydrolysis

34. Try to draw the following product in your notebook…

35. Note: the “group” of the alcohol is the “group” on the oxygen of the ester! 

36. Try to draw the following product in your notebook…

37. Remember, redraw the “acid” side, then add the “R” group of the alcohol to the oxygen of the ester… 

38. Try to draw the following product in your notebook…(there is a hint on the next slide)

39. Remember, you’re adding water to the ester to “break” it back into the acid and alcohol…

40. The acid breaks apart into the acid and alcohol.

41. Try to draw the following product in your notebook…(no color coordination this time, though)! 

42. There are 5 carbons in the acid and 2 in the alcohol

43. Base Hydrolysis (Saponification)
Base hydrolysis (also called saponification)
is the reaction of an ester with a strong base.
produces the salt of the carboxylic acid and an alcohol.

44. “Soaps”
The base hydrolysis of long-chain fatty acids produces acid salts called “soaps.”

45. Cleaning Action of Soap
A soap
contains a nonpolar end that dissolves in nonpolar fats and oils and a polar end that dissolves in water.
forms groups of soap molecules called micelles that dissolve in water and are washed away.
Micelles can take various forms,
but this is pretty common…

46. “Trapping” Action of Soap
Oil and grease are “trapped” inside the hydrophobic part of the micelle…

47. Soaps vs. Detergents Soaps contain a carboxylic acid
Detergents contain a sulfur
Sulfur doesn’t form bonds with the Ca+2 ions in water, so more is
Available to “encase” the dirt on clothing…

48. Learning Check
Give the following product…

49. Learning Check
Remember that the water breaks the ester apart into the acid & alcohol…

50. Learning Check
Give the following product…

51. Learning Check
This is basically the same thing, but the acid is a salt since it is in a basic solution…

52. Comparing the acid and base products…