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Natural Products Nomenclature Acidity Preparation Reactions

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Presentation on theme: "Natural Products Nomenclature Acidity Preparation Reactions"— Presentation transcript:

1 Natural Products Nomenclature Acidity Preparation Reactions
Carboxylic Acids Natural Products Nomenclature Acidity Preparation Reactions

2 Analgesics

3 Fats and Fatty Acids

4 From Ergot Fungus

5 Common Nomenclature

6

7 I.U.P.A.C. Nomenclature

8 Dicarboxylic Acids

9 A Diacid

10 Unusually High Melting and Boiling Points

11 Boiling Points

12 Acidity is due to Delocalization of the Charge in the Conjugate Base

13 Alcohol vs. Acid

14 e- Withdrawing Groups Enhance Acidity

15 Benzoic acids

16 Deprotonation

17 Carboxylic Acid Preparations
Oxidation of 1o alcohols and aldehydes with Na2Cr2O7/H2SO4 KMnO4 oxidation of alkylbenzenes Hydrolysis of a carboxylic derivative: e.g. acid chloride, acid anhydride, ester, amide, nitrile

18 Carboxylic Acid Derivatives
Acid Chlorides Acid Anhydrides Esters Amides Nitriles Nucleophilic Acyl Substitution

19 Reactivity of Acid Derivatives

20

21 Acid Chloride Preparation

22

23 I.U.P.A.C. Nomenclature (uses carboxylic acid template)

24 Acid Chlorides

25 Acid Anhydrides

26 Esters

27 Amides

28 All Acid Derivatives can be Hydrolyzed

29 What are the 3 Hydrolysis Products?

30

31 Draw the Hydrolysis Products

32 Hydrolysis of Penicillin

33 Aspartame

34 Nucleophilic Acyl Substitution

35 Nucleophilic Acyl Substitution

36 Hydrolysis of an Acid Chloride

37 With Acid Chlorides, No Catalyst is Needed Anhydride Prep.

38

39 Ester Preparation from an acid chloride

40 Amide Preparation from an Acid Chloride

41 Amide from Anhydride

42 Proteins are amides!

43 Fischer Esterification

44 Flavors and Fragrances

45 Basic Hydrolysis Saponification

46 Basic Hydrolysis of an Amide

47 Mechanism

48

49 Reduction of Esters with LiAlH4

50 Due 15Mar 5 pm @RAM pigeonbox
10.33 a, d


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