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Question 71 of 76

Q.The oxidising agent used to stop the oxidation of primary alcohol at the aldehyde stage is :

(a) Na2Cr2O7Na_2Cr_2O_7
(b) KMnO4KMnO_4
(c) K2Cr2O7K_2Cr_2O_7
(d) PCC
Puducherry TnboardTamil Nadu HSC (DGE) Board 2024MCQ· 1mImportance★★★★★
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PCC (pyridinium chlorochromate) is a mild, anhydrous chromium(VI) oxidant that stops the oxidation of a primary alcohol exactly at the aldehyde stage, whereas KMnO4KMnO_4/Na2Cr2O7Na_2Cr_2O_7/K2Cr2O7K_2Cr_2O_7 in aqueous acidic medium drive the oxidation all the way to the carboxylic acid.

Oxidation of a primary alcohol, R−CH2OHR-CH_2OH, can in principle proceed in two steps: first to the aldehyde (R−CHOR-CHO), and then, if water/excess strong oxidant is present, further to the carboxylic acid (R−COOHR-COOH). Strong aqueous oxidants such as acidified KMnO4KMnO_4, K2Cr2O7K_2Cr_2O_7, or Na2Cr2O7Na_2Cr_2O_7 readily drive the reaction all the way to the carboxylic acid, because water is required for/present during the aldehyde-to-acid oxidation step, and these reagents are vigorous oxidants. Pyridinium chlorochromate (PCC, C5H5NH+CrO3Cl−C_5H_5NH^+CrO_3Cl^-), by contrast, is used in an anhydrous, non-aqueous medium (typically dichloromethane) and is a comparatively mild chromium(VI) oxidant — since no water is present to hydrate the aldehyde intermediate (a step needed b …

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