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Properties Nomenclature Preparation Reactions Synthesis

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Presentation on theme: "Properties Nomenclature Preparation Reactions Synthesis"— Presentation transcript:

1 Properties Nomenclature Preparation Reactions Synthesis
Ketones and Aldehydes Properties Nomenclature Preparation Reactions Synthesis

2 Carbonyl Functional Groups

3 Large Dipole Controls Properties and Reactivity

4 Boiling Points Dipole-Dipole Interactions

5 Adrogenic/Anabolic Steroids

6 Anabolic Steroids

7 IUPAC Nomenclature Ketones

8

9 IUPAC Nomenclature Aldehydes

10 Preparation of Ketones and Aldehydes
Friedel-Crafts Acylation (ketones) Hydration of Alkynes (ketones with oxymercuration, aldehydes with hydroboration) Ozonolysis of Alkenes (aldehydes and ketones depending on Reduction of acids, acid chlorides and nitriles Oxidation of alcohols

11 Friedel-Crafts Acylation

12 Isoflavones Highly Sought After Natural Products

13

14 Acylation occurs ortho to OH

15 Oxymercuration Hydration Markovnikov

16 Hydroboration Hydration Anti-Markovnikov

17 Ozonolysis Alkene Cleavage

18 DIBAH Diisobutyl Aluminum Hydride

19 Nucleophilic Addition Reactions: Strong Nucleophiles

20 Carbonyl Reactivity

21 NaBH4 Reduction

22 Some Examples

23 Grignard Reagents React With Ketones to form tertiary alcohols

24 Grignard Summary

25 Nucleophilic Addition Reactions: Weak Nucleophiles

26 Acetal Formation

27 Acetal Mechanism

28 Use of Ethylene Glycol to Protect Ketones and Aldehydes

29 Synthesis

30 Synthesis

31 Aldehydes React Preferentially

32 Imine Formation

33 Imines and Enamines

34

35 Enamine Mechanism (same as imine mech. until last step)

36 Imine Derivatives

37 Conjugate Addition to a,b-Unsaturated C=O groups

38 1,2- vs. 1,4-Addition

39 Gilman Reagents add 1,4

40 Synthesis

41 Carry Out Conjugate Addition 1st

42 Propose a Sequence of Steps…

43 Enols and Enolates a Substitutions and Condensations of Ketones and Aldehydes

44 Tautomerization Accelerated in Acid

45 Reaction Occurs via Enol

46 Tautomerization Acceleration in Base

47 Alkylation in Base Reaction with 1o RX


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