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Lecture 6 - Carboxylic Acids

Lecture 6 - Carboxylic Acids - BME 201 Carboxylic acids...

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1 BME 201 Carboxylic acids, Esters and Derivatives Suggested problems review material: Vollhardt, Chapter 19, problems no. 27, 28, 29 exercise 19.1 Todays lecture is based on Vollhardt, selected materials from chapters 19 and 20 ( carboxylic acids, esters and other derivatives ) as well as selected handouts. Handouts may have marked chapter numbers and page numbers for suggested reading. You will find it easier to do the suggested problems and pass future quizzes and exams if you go over the reading prior to attempting to solve the suggested problems.
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2 Carboxylic Acids
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3 Naming the Carboxylic Acids 19-1 Chemical Abstracts retains the common names for the two simplest  carboxylic acids, formic acid and acetic acid. The IUPAC system derives the name of carboxylic acids by replacing the  ending –e in the parent alkane by the ending  –oic acid .
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4 The alkanoic acid stem is numbered by assigning 1 to the carbonyl carbon  and labeling any substituents along the longest chain incorporating the  CO 2 H group accordingly.
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5 The carbonyl group and the functional groups of its derivatives take  precedence in naming over any other groups discussed so far:
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6 When other functional groups are present, the main chain is chosen to  include other functional groups as much as possible. Saturated cyclic acids are named as  cycloalkanecarboxylic acids . Aromatic acids are named  benzoic acids . Dicarboxylic acids are referred to as  dioic acids .
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7 Structural and Physical Properties of Carboxylic Acids 19-2 Formic acid is planar. The molecular structure of formic acid is roughly planar, which is  characteristic of carboxylic acids in general.
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8 The carboxy group is polar and forms   hydrogen-bonded dimers.
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9
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10
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11 Acidic and Basic Character of Carboxylic Acids 19-4 Carboxylic acids are relatively strong acids.
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12 Electron-withdrawing substituents increase the acidity of  carboxylic acids.
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13 Carboxylate salts of carboxylic acids can be prepared by treatment of the  acid with a base, such as NaOH, Na 2 CO 3  or NaHCO 3 . These salts are  much more water soluble than the corresponding acids.
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14 Carboxylic acids may be protonated on the carbonyl oxygen. The carbonyl oxygen of a carboxylic acid may be protonated by strong  acids to give alkyloxonium ions. The carbonyl oxygen is more basic than the –OH group of alcohols due to  resonance stabilization of the alkyloxonium ion. Note that the protonation reaction is not particularly strong.
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15 Carboxylic Acid Synthesis in Industry 19-5 Formic acid and acetic acid are manufactured on a large scale industrially.
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16 Methods for Introducing the Carboxy Functional Group 19-6 Oxidation of primary alcohols and of aldehydes furnishes  carboxylic acids.
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