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Swern Oxidation (rxn not in aqueous solution)

Oxidative Cleavage

Only D cannot be cleaved by periodic acid acid.

Oxidative Cleavage by Alkenes

What Stereoisomers are obtained from the following reactions? • • • • • • • •

trans-2-butene + HBr (Z)-3-methyl-2-pentene + HBr (E)-3-methyl-2-pentene + HBr Cis-3-hexene + HBr Cis-2-pentene + Br2 1-hexene + Br2 1,2-dimethylcyclohexene + KMnO4/OH- (cold) 1,2-dimethylcyclohexene + MCPBA

1. When one mole of each of the following compounds is treated with HIO4, what will the product be, and how many moles of HIO4 will be consumed? a.CH3CHOHCH2OH b. CH3CHOHCHO c. CH2OHCHOHCH2OCH3 2. Assign a structure to each of the following A + 1 mol HIO4 --- HOOC(CH2)4CHO • b. B + 1 mol HIO4 --- 2HOOC-CHO c. C + 3 HIO4 --- 2HCOOH + 2HCHO d. D + 3 HIO4 - 2 HCOOH + HCHO + CO2 e. E + 5 HIO4 - 5 HCOOH + HCHO f. F + 4 HIO4 -- 3HCOOH + HCHO + OHC-COOH g. G + 5HIO4 -- 4 HCOOH + 2 HCHO