TAILIEUCHUNG - Lecture Organic chemistry - Chapter 19: Carboxylic acids

Lecture Organic chemistry - Chapter 19: Carboxylic acids. The following will be discussed in this chapter: Naming: alkanoic acids, resonance, acidity, oxidation of primary alcohols and aldehydes, carbonation: organometallic reagents and carbon dioxide, nitrile hydrolysis,.and other contents. | Chapter 19: Carboxylic Acids Carboxy group: -COOH, -CO2H, Carboxylic acids take precedence over other groups: Naming: Alkanoic Acids IUPAC: Replace –e of alkane name with –oic acid 4-Methylhexanoic acid C1 Cyclic: Cycloalkanecarboxylic acids Cyclohexanecarboxylic acid 1-Naphthalenecarboxylic acid C1, as in cyclic aldehydes HCOOH Methanoic acid—Formic acid accepted CH3COOH Ethanoic acid—Acetic acid accepted CH3CH2COOH Propanoic acid Etc. Resonance Ketones versus Carboxylic Acids: Acidity The carboxy group is relatively acidic: Acetate ion Reasons: 1. Carbonyl carbon is inductively strongly electron withdrawing, 2. Carboxylate ion is stabilized by resonance Compare 2-Propenyl (allyl) BH + pKa ~ 40 + Electron withdrawing groups increase the acidity (decrease pKa): Distance affects acidity: pKa pKa CH3COOH pKa = CF3COOH pKa = Basicity Protonated on the carbonyl oxygen: Allows for allylic resonance 1. Oxidation of primary alcohols and aldehydes With KMnO4; or CrO3, .

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