Question

Which is not a product of oxidation of citral with KMnO4 and CrO3?

• A. Oxalic acid
• B. Acetone
• C. Leavulic acid
• D. Acetaldehyde

Hint:

Break citral at both its double bonds and see which small fragments are actually generated.

Answer 1

The Correct Option is D

Step 1: Citral is 3,7-dimethylocta-2,6-dienal, with an isopropylidene double bond at C6-C7 and a double bond at C2-C3 conjugated with the aldehyde.

Step 2: Cleavage of the C6-C7 double bond gives acetone, (CH3)2C=O.

Step 3: Cleavage of the C2-C3 double bond gives a two-carbon fragment OHC-COOH, further oxidized to oxalic acid.

Step 4: The remaining fragment is levulinic acid, CH3-CO-CH2-CH2-COOH.

Step 5: Acetaldehyde would need a terminal =CH-CH3 fragment, but citral has no such fragment, so acetaldehyde is never generated.

\[\boxed{\text{Acetaldehyde is not a product}}\]