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Published byBlaise Osborne Caldwell Modified over 6 years ago
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Properties Nomenclature Preparation Reactions Synthesis
Ketones and Aldehydes Properties Nomenclature Preparation Reactions Synthesis
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Carbonyl Functional Groups
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Large Dipole Controls Properties and Reactivity
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Boiling Points Dipole-Dipole Interactions
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Adrogenic/Anabolic Steroids
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Anabolic Steroids
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IUPAC Nomenclature Ketones
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IUPAC Nomenclature Aldehydes
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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
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Friedel-Crafts Acylation
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Isoflavones Highly Sought After Natural Products
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Acylation occurs ortho to OH
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Oxymercuration Hydration Markovnikov
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Hydroboration Hydration Anti-Markovnikov
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Ozonolysis Alkene Cleavage
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DIBAH Diisobutyl Aluminum Hydride
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Nucleophilic Addition Reactions: Strong Nucleophiles
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Carbonyl Reactivity
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NaBH4 Reduction
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Some Examples
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Grignard Reagents React With Ketones to form tertiary alcohols
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Grignard Summary
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Nucleophilic Addition Reactions: Weak Nucleophiles
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Acetal Formation
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Acetal Mechanism
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Use of Ethylene Glycol to Protect Ketones and Aldehydes
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Synthesis
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Synthesis
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Aldehydes React Preferentially
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Imine Formation
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Imines and Enamines
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Enamine Mechanism (same as imine mech. until last step)
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Imine Derivatives
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Conjugate Addition to a,b-Unsaturated C=O groups
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1,2- vs. 1,4-Addition
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Gilman Reagents add 1,4
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Synthesis
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Carry Out Conjugate Addition 1st
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Propose a Sequence of Steps…
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Enols and Enolates a Substitutions and Condensations of Ketones and Aldehydes
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Tautomerization Accelerated in Acid
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Reaction Occurs via Enol
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Tautomerization Acceleration in Base
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Alkylation in Base Reaction with 1o RX
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