Ketones and Aldehydes 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) • Reduction of acids, acid chlorides and nitriles • Oxidation of alcohols

Friedel-Crafts Acylation

Oxymercuration Hydration Markovnikov

Hydroboration Hydration Anti-Markovnikov

DIBAH Diisobutyl Aluminum Hydride

Reduction Summary DIBAH [O] w/ PCC or Periodinane

How would you prepare the ff? 1. Pentanal from: a. pentan-1 -ol b. De-5 -ene c. Pentanoic acid 2. Hexan-2 -one from: a. hexan-2 -ol b. 2 -methyl-hex-1 -ene c. 1 -hexyne

Oxidation - Reduction

Oxidation Summary Cr. O 3, H 3 O+

Nucleophilic Addition Reactions: Strong Nucleophiles

Na. BH 4 Reduction

Some Examples

Grignard Reagents React With Ketones to form tertiary alcohols

Grignard Summary

How would you prepare the ff using a Grignard reagent? 1. 2. 3.

Nucleophilic Addition Reactions: Weak Nucleophiles

Acetal Formation

Acetal Mechanism

Use of Ethylene Glycol to Protect Ketones and Aldehydes

Synthesis

Synthesis

Aldehydes React Preferentially

Carbonyl compounds with alpha hydrogens are (surprisingly) slightly acidic. Why?

The conjugate base is stabilized by resonance! Draw the resonance forms for the conjugate base.

Identify the most acidic proton: 1. 2. 3. 4. cyclohexane-1, 3 -dione Propanal Acetic acid 3, 3 -dimethylbutan-2 -one

Aldol Condensation Dimerization of 3 -Pentanone