Please provide mechanisms for these reactions Compound 5 (shown below) displays intriguing reactivity features at distinct pHs. We willexplore several examples.OHO.рH 13OHОН ОLIOH78H2OОН ООН ОН56pH 7+ CO2HOОН ОНОН О10(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 reasonablemechanism for this reaction.OHOHLIOHpH 13O.H2OОн ООН О78Hints: a somewhat challenging pathway; start with Aldol chemistry and recall the extremepH! 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. Proposea reasonable mechanism for this reaction.OHОН ОНLIOHpH 7HO+ CO2H2OÓH ÖОН ОНОН О510

(a) In highly basic condition, the following mechanism can take place

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

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...

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