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Orgo 2213 Topic 10a Notes.docx

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Department
Chemistry
Course
Chemistry 1027A/B
Professor
Mel Usselman
Semester
Fall

Description
Key Concepts In Organic Chemistry: Carboxylic Acids (Usselman Version) -The carboxylic acid functional group results from the connection of a carbonyl functional group to a hydroxyl group. This implies the fact that carboxylic acids will do hydroxyl reactions, carbonyl group reactions and the OH can function as a good LG if protonated. In IUPAC nomenclature, the COOH is always given priority, the C of the COOH is #1, and the –e in the word “alkane” is changed to –oic acid. The very simple acids are known by their common names (formic acid, acetic acid and oxalic acid). If a molecule contains a C = 0 in addition to an acyl group, its position is noted by the prefix oxo. -In carboxylic acids, the polar bonds are located at one end of the molecule, termed the hydrophilic end, which strongly interacts with water. The other end of the molecule with the R group, termed the hydrophobic end, is non-polar and has very low solubility in water. -The IR spectrum of carboxylic acids contains two strong, characteristic peaks: a C = O peak at 1700- -1 -1 1752cm and a very broad OH peak at 2400-3400cm . In proton NMR, the acidic H of the carboxylic acid group appears far downfield (to the left) at δ = 10-13. -On exposure to bases, carboxylic acids react to form water-soluble salts (they are strong, organic weak acids). Carboxylic acids are easily prepared by the oxidation of 1° alcohols and aldehydes (except when PCC is used as the oxidizing agent). -In the reduction to 1° alcohols reaction, other reducing agents that hydrogenate alkenes and carbonyl groups (such as NaBH ) 4re used which do not affect carboxylic acid groups. -Carboxylic acids th
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