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Animated Solution for Chemistry - Carbonyl Compounds: On vigorous oxidation by permangnate solution gives

Select Answer:

Visualized Solution

  • Reactant:
  • Reagent: (Vigorous Oxidation)

  • Role of :
  • 1. Cleaves bond.
  • 2. Oxidises to .

  • Cleavage of bond:
  • Left fragment: (Acetone)

  • Oxidation of right fragment:
  • (Malonic acid)

  • Final Products:
  • 1.
  • 2.

  • What would be the product if reductive ozonolysis () was used instead?

The Sigma Insight: Types of Organic Reactions

Solution Diagram

The Power of Potassium Permanganate

Imagine you are a molecular surgeon, and your scalpel is potassium permanganate (). When we talk about "vigorous oxidation" using , we are not talking about a gentle nudge. We are talking about a powerful chemical transformation that aggressively attacks specific vulnerabilities in a molecule.
In our reactant, , there are two primary targets for this aggressive oxidizing agent: the carbon-carbon double bond () and the aldehyde group ().

Cleaving the Double Bond

The first major event is the oxidative cleavage of the double bond. acts like a pair of molecular scissors, completely snapping the bond in half.
Let's look at the left fragment after the snap: . Because this carbon atom is bonded to two methyl groups and has no hydrogen atoms attached to it, it gets capped with an oxygen atom to form a stable ketone. Specifically, it forms acetone, . Ketones are tough; they resist further oxidation under these conditions, so this part of the molecule is done reacting.

Oxidizing the Aldehyde

Now, let's turn our attention to the right fragment: . This part is in for a double whammy.
First, the carbon that was part of the double bond () gets oxidized. Because it has a hydrogen atom attached, it doesn't stop at an aldehyde; it gets fully oxidized into a carboxylic acid group ().
Second, the molecule already had an aldehyde group () at the other end. makes quick work of this as well, oxidizing it straight into another carboxylic acid group.
The group in the middle is relatively unreactive and stays intact. So, the entire right fragment transforms into a dicarboxylic acid: , which is commonly known as malonic acid.

The Final Verdict

By carefully analyzing the action of vigorous on both reactive sites, we've successfully predicted the outcome. The molecule splits and oxidizes to give us two distinct products: acetone and malonic acid.
Therefore, the final products are and . This perfectly matches option (d).
Always remember: strong oxidizing agents don't just break bonds; they push every reactive carbon to its highest possible oxidation state!

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