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Ch 19 Orgo 2 Mechanisms
1.
Formation of Hemiacectal (vinyl ether forms it as well)
Product: OH and OR
Reagent: R OH
2.
Formation Acetal
Product: OR & OR
Reagent: R OH /H
3.
Hydrolysis to Regenerate Carbonyl and Alcohol Constituents
Product: Any carbonyl group; alcohol group
Reagent: H3O+
4.
Thioacetal formation
Product: SR SR
Reagent: RSH/ ZnCl2
5.
Thioacetal Hydrolysis
Product: Ketones and other carbonyl groups
Reagent: HgCl2, CaCo3/ H2O, CH3CN
6.
Desulfurization
Product: More hydrogens
Reagent: Raney Ni
7.
Carbohydrates undergo reduction to form alditols
Product: OH - H or H - OH
Reagent: NaBH4/ EtOH
8.
Carbohydrates undergo oxidation to form Aldonic acid
Product: CooH (1)
Reagent: Br2/H2O
9.
Carbohydrates undergo oxidation to form aldaric acids
Product: COOH (2)
Reagent: HNO3
