Chem.62.Chapt17 - Chapter 17-1 Carboxylic Acids Chem 62...

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Chapter 17-1 Chem 62 Carboxylic Acids Carboxylic acids contain both a carbonyl and a hydroxyl function R C O O : R C O O—H R C O O C O O R .. . . . . .. .. H + + . . . . .. .. .. .. . . . . C O H R H O: :O: C O R carboxylic acid dimer: results in higher melting and boiling points Spectral Properties —OH stretch in the infrared is intense due to dimers...3300 - 3000 C=O stretch 1700 - 1725 shifted to 1680 - 1700 if conjugated —COOH in 1H NMR at about 10 - 13 ppm as a broad singlet Preparation 1. Hydrolysis of carboxylic acid derivatives 2. oxidation of alcohols, aldehydes, or alkenes 3. Grignard reactions Hydrolysis of Carboxylic acid derivatives CH 3 C O O—CH 2 CH 3 CH 3 C O O—H CH 3 C O Cl CH 3 C O O CH 3 C O also yield acetic acid on hydrolysis CH 3 C N H 2 O, H + or HO - + HOCH 2 CH 3 Oxidation CH 2 OH COOH alcohols H 2 CrO 4 H 2 CrO 4 CH 3 CH 2 CH 2 COOH CH 3 CH 2 CH 2 CH 2 OH
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Chapter 17-2 Chem 62 Carboxylic Acids CH 3 COOH CH 3 CH 2 CH 2 COOH loss of one carbon 1. O 3 2. H 2 O 2 alkenes aldehydes benzylic carbons Grignard Reaction Reaction of a Grignard reagent with CO 2 yields a carboxylate salt...acidification produces a carboxylic acid with one additional carbon 1. Mg 2.CO 2 3. H + CH 3 CH 2 CH 2 COOH addition of one carbon CH 3 CH 2 CH 2 Mg + Br C O O H 3 C O Mg + Br O H 3 O + H 3 C OH O CH 3 CH 2 CH 2 CH=CH 2 CH 3 COOH H 2 CrO 4 CH 3 CHO KMnO 4 H + CO 2 Mg CH 3 CH 2 CH 2 COO - + MgBr CH 3 CH 2 CH 2 MgBr CH 3 CH 2 CH 2 Br
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Chapter 17-3 Chem 62 Carboxylic Acids ACIDITY R—CH 3 R—NH 2 RC C—H RO—H 15-19 H2O 15.7 ArO—H 10 H 2 CO 3 6.4 R—CO 2 H 5 45-50 35 25 15-19 15.7 10 6.4 5 Approximate pKa Acid strength: extent of ionization of a Bronstead acid in water the greater the ionization, the greater the acidity H 3 O + + A - HA + H 2 O Anything that stabilizes the anion (A-) will increase the acidity of HA Factors which affect acidity 1. electronegativity of the atom carrying the charge (A-)
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  • Spring '08
  • Forbes
  • Chem, Carboxylic acid

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