Question:medium

Which one of the following reactions will not yield propionic acid ?

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Remember the standard methods for synthesizing carboxylic acids: oxidation of primary alcohols and aldehydes, hydrolysis of nitriles or esters, hydrolysis of gem-trihalides, Grignard carboxylation, and the haloform reaction for methyl ketones. Knowing the carbon count change in each reaction is crucial (e.g., Grignard carboxylation adds one carbon).
Updated On: Feb 18, 2026
  • CH\(_3\)CH\(_2\)CH\(_3\) + KMnO\(_4\)(Heat), OH\(^-\)/H\(_3\)O\(^+\)
  • CH\(_3\)CH\(_2\)CCl\(_3\) + OH\(^-\)/H\(_3\)O\(^+\)
  • CH\(_3\)CH\(_2\)COCH\(_3\) + OI\(^-\)/H\(_3\)O\(^+\)
  • CH\(_3\)CH\(_2\)CH\(_2\)Br + Mg, CO\(_2\) dry ether/H\(_3\)O\(^+\)
Show Solution

The Correct Option is A

Solution and Explanation

To solve the given problem of which reaction will not yield propionic acid (CH3CH2COOH), let's analyze each provided option:

  1. CH3CH2CH3 + KMnO4(Heat), OH-/H3O+
    • Propan-1-yl (CH3CH2CH3) subjected to strong oxidation with KMnO4 does not usually yield propionic acid. Instead, alkanes typically undergo oxidation to form a mixture of products including carbon dioxide and water, rather than a specific carboxylic acid, especially when heated and oxidized aggressively like in this condition.
  2. CH3CH2CCl3 + OH-/H3O+
    • This is a typical haloform reaction. The trichloromethyl group (CCl3) in a haloform reaction specifically leads to the formation of a carboxylic acid from the homologous ketone. This can yield propionic acid from precursors containing the appropriate alkyl groups.
  3. CH3CH2COCH3 + OI-/H3O+
    • This reaction represents the oxidation of a ketone (2-butanone) using typical conditions that can oxidize alpha-hydroxy ketones to their corresponding carboxylic acids. This should yield propionic acid through oxidative cleavage and formic acid as a byproduct.
  4. CH3CH2CH2Br + Mg, CO2 dry ether/H3O+
    • This describes the Grignard reaction. CH3CH2CH2Br reacted with Mg in dry ether forms a Grignard reagent. Reacting with CO2 and further hydrolyzation with acid typically leads to the formation of propionic acid.

Considering the explanations above, the reaction described in option 1 does not directly form propionic acid. Thus, the answer is:

CH3CH2CH3 + KMnO4(Heat), OH-/H3O+

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