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

Carbonyl Functional Groups

Large Dipole Controls Properties and Reactivity

Boiling Points Dipole-Dipole Interactions

Adrogenic/Anabolic Steroids

Anabolic Steroids

IUPAC Nomenclature Ketones

IUPAC Nomenclature Aldehydes

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

Friedel-Crafts Acylation

Isoflavones Highly Sought After Natural Products

Acylation occurs ortho to OH

Oxymercuration Hydration Markovnikov

Hydroboration Hydration Anti-Markovnikov

Ozonolysis Alkene Cleavage

DIBAH Diisobutyl Aluminum Hydride

Nucleophilic Addition Reactions: Strong Nucleophiles

Carbonyl Reactivity

NaBH4 Reduction

Some Examples

Grignard Reagents React With Ketones to form tertiary alcohols

Grignard Summary

Nucleophilic Addition Reactions: Weak Nucleophiles

Acetal Formation

Acetal Mechanism

Use of Ethylene Glycol to Protect Ketones and Aldehydes

Synthesis

Synthesis

Aldehydes React Preferentially

Imine Formation

Imines and Enamines

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

Imine Derivatives

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

1,2- vs. 1,4-Addition

Gilman Reagents add 1,4

Synthesis

Carry Out Conjugate Addition 1st

Propose a Sequence of Steps…

Enols and Enolates a Substitutions and Condensations of Ketones and Aldehydes

Tautomerization Accelerated in Acid

Reaction Occurs via Enol

Tautomerization Acceleration in Base

Alkylation in Base Reaction with 1o RX