Q1 Cont'd:c) While the oxidation of alcohol 2 using Jone's reagent produces carboxylic acid3, the oxidation of 2 using the Collin's reagent (Pyridinium ChloroChromate PCCin anhydrous CH2Cl2 as the solvent) stops at the aldehyde 4. Provide a detailedarrow pushing mechanism for the oxidation of alcohol 2 to aldehyde 4.3CO₂HJone's reagentCrO3, H,SO4acetone/H202Collin's reagentPCC:C---H-N*anhydrous CH2Cl2CHOΤΗd) Explain why the oxidation of aldehyde 4 does not proceed further under theCollin's oxidation conditions to produce acid 3. a) Provide the product for the oxidation of compound 1 using the Jone's reagent(CrO3 and H2SO4 in a mixture of acetone and water as the solvent).OHOHCrO3, H2SO4acetone/H20b) Provide a detailed arrow-pushing mechanism for Jone's oxidation of theprimary alcohol in compound 1 to its final oxidized state in the product.

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Answered: Q1 Cont'd: c) While the oxidation of…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.5: Nucleophilic Addition Of H2o: Hydration

Problem 7P

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