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Question

Chemistry Question on Alcohols

The most suitable reagent for the conversion of RCH2OHRCHORCH_2OH \to RCHO is

A

KMnO4KMnO_4

B

K2Cr2O7K_2Cr_2O_7

C

CrO3CrO_3

D

PCCPCC (pyridine chloro chromate)

Answer

PCCPCC (pyridine chloro chromate)

Explanation

Solution

Pyridinium chlorochromate (PCC) (C5H5NHCrO3Cl)\left( C _{5} H _{5} NHCrO _{3} Cl ^{-}\right)is a very good oxidising agent for converting 11^{\circ} alcohol to aldehydes and 22^{\circ} alcohols to ketone. It prevents further oxidation of aldehydes to carboxylic acid.
RCH2OHp-alcoholCH2Cl2solvent(CH2H5N)2CrO3RCHOAldehyde+H2O\underset{\text{p-alcohol}}{RCH_2OH} \xrightarrow[CH_2Cl_2 \text{solvent}]{(CH_2H_5N)_2CrO_3} \underset{\text{Aldehyde}}{RCHO} + H_2O
[PCC is prepared by mixing pyridine (C5H5N),CrO3\left( C _{5} H _{5} N \right), CrO _{3} and HClHCl.
ROH acidified K2Cr2O7alkalineKMnO4orROH \xrightarrow[\text { acidified } K _{2} Cr _{2} O _{7}]{\text{alkaline} KMnO_4 or} Carboxylic acid
ROHCrO3/CH3COOHROH \xrightarrow{ CrO _{3} / CH _{3} COOH } aldehyde