Q1 Cont'd: c) While the oxidation of alcohol 2 using Jone's reagent produces carboxylic acid 3, the oxidation of 2 using the Collin's reagent (Pyridinium ChloroChromate PCC in anhydrous CH2Cl2 as the solvent) stops at the aldehyde 4. Provide a detailed arrow pushing mechanism for the oxidation of alcohol 2 to aldehyde 4. 3 CO₂H Jone's reagent CrO3, H,SO4 acetone/H20 2 Collin's reagent PCC: C--- H-N* anhydrous CH2Cl2 CHO ΤΗ d) Explain why the oxidation of aldehyde 4 does not proceed further under the Collin'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). OH OH CrO3, H2SO4 acetone/H20 b) Provide a detailed arrow-pushing mechanism for Jone's oxidation of the primary alcohol in compound 1 to its final oxidized state in the product.

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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Q1 Cont'd:
c) While the oxidation of alcohol 2 using Jone's reagent produces carboxylic acid
3, the oxidation of 2 using the Collin's reagent (Pyridinium ChloroChromate PCC
in anhydrous CH2Cl2 as the solvent) stops at the aldehyde 4. Provide a detailed
arrow pushing mechanism for the oxidation of alcohol 2 to aldehyde 4.
3
CO₂H
Jone's reagent
CrO3, H,SO4
acetone/H20
2
Collin's reagent
PCC:
C---
H-N*
anhydrous CH2Cl2
CHO
ΤΗ
d) Explain why the oxidation of aldehyde 4 does not proceed further under the
Collin's oxidation conditions to produce acid 3.
Transcribed Image Text:Q1 Cont'd: c) While the oxidation of alcohol 2 using Jone's reagent produces carboxylic acid 3, the oxidation of 2 using the Collin's reagent (Pyridinium ChloroChromate PCC in anhydrous CH2Cl2 as the solvent) stops at the aldehyde 4. Provide a detailed arrow pushing mechanism for the oxidation of alcohol 2 to aldehyde 4. 3 CO₂H Jone's reagent CrO3, H,SO4 acetone/H20 2 Collin's reagent PCC: C--- H-N* anhydrous CH2Cl2 CHO ΤΗ d) Explain why the oxidation of aldehyde 4 does not proceed further under the Collin'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).
OH
OH
CrO3, H2SO4
acetone/H20
b) Provide a detailed arrow-pushing mechanism for Jone's oxidation of the
primary alcohol in compound 1 to its final oxidized state in the product.
Transcribed Image Text: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). OH OH CrO3, H2SO4 acetone/H20 b) Provide a detailed arrow-pushing mechanism for Jone's oxidation of the primary alcohol in compound 1 to its final oxidized state in the product.
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