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NEET CHEMISTRYMedium

The compound (structure missing) on reaction with NaIO4\text{NaIO}_4 in the presence of KMnO4\text{KMnO}_4 gives:

A

CH3COCH3\text{CH}_3\text{COCH}_3

B

CH3COCH3+CH3COOH\text{CH}_3\text{COCH}_3 + \text{CH}_3\text{COOH}

C

CH3COCH3+CH3CHO\text{CH}_3\text{COCH}_3 + \text{CH}_3\text{CHO}

D

CH3CHO+CO2\text{CH}_3\text{CHO} + \text{CO}_2

Step-by-Step Solution

The combination of sodium periodate (NaIO4\text{NaIO}_4) and a catalytic amount of potassium permanganate (KMnO4\text{KMnO}_4) is known as the Lemieux-von Rudloff reagent. It acts as a strong oxidizing agent used for the oxidative cleavage of carbon-carbon double bonds. The reaction yields products similar to oxidative ozonolysis or oxidation by hot acidic KMnO4\text{KMnO}_4 .

In this process, an alkene carbon bonded to two alkyl groups is oxidized to a ketone, while an alkene carbon bonded to one alkyl group and one hydrogen atom is oxidized to a carboxylic acid (the intermediate aldehyde is further oxidized by KMnO4\text{KMnO}_4). To obtain acetone (CH3COCH3\text{CH}_3\text{COCH}_3) and acetic acid (CH3COOH\text{CH}_3\text{COOH}), the original missing compound must have been 2-methylbut-2-ene (CH3-C(CH3)=CH-CH3\text{CH}_3\text{-C(CH}_3\text{)=CH-CH}_3).

Note: The specific chemical structure of the reactant was missing from the input data. Option 2 is marked correct based on the provided probable answer.

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