Compound 5 (shown below) displays intriguing reactivity features at distinct pHs. We will explore several examples. OH pH 13 OH ОН О LIOH 7 8 H20 ОН О ОН ОН pH 7 + CO2 HO ОН ОН ÓH Ö 10 (a) When 5 and 6 are treated with LIOH and the pH is further adjusted to highly basic (pH 13–14), products 7 and 8 are predominantly formed. Propose a reasonable mechanism for this reaction. OH OH LIOH рH 13 H H2O ÓH O ÓH Ö 7 Hints: a somewhat challenging pathway; start with Aldol chemistry and recall the extreme pH! You may be able to “take advantage" of intramolecular H transfer. (b) When 5 and 6 are treated with LIOH and the pH is further adjusted close to neutral (pH 6–8), products 9 and 10 (in addition to CO2) are predominantly formed. Propose a reasonable mechanism for this reaction. OH ОН ОН LIOH pH 7 H H20 но + CO2 О ОН ОН OH O 6 10
Compound 5 (shown below) displays intriguing reactivity features at distinct pHs. We will explore several examples. OH pH 13 OH ОН О LIOH 7 8 H20 ОН О ОН ОН pH 7 + CO2 HO ОН ОН ÓH Ö 10 (a) When 5 and 6 are treated with LIOH and the pH is further adjusted to highly basic (pH 13–14), products 7 and 8 are predominantly formed. Propose a reasonable mechanism for this reaction. OH OH LIOH рH 13 H H2O ÓH O ÓH Ö 7 Hints: a somewhat challenging pathway; start with Aldol chemistry and recall the extreme pH! You may be able to “take advantage" of intramolecular H transfer. (b) When 5 and 6 are treated with LIOH and the pH is further adjusted close to neutral (pH 6–8), products 9 and 10 (in addition to CO2) are predominantly formed. Propose a reasonable mechanism for this reaction. OH ОН ОН LIOH pH 7 H H20 но + CO2 О ОН ОН OH O 6 10
Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
Problem 37AP
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