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Question

The correct order for the relative rate of esterification of I, II, and III with p-nitrobenzoyl chloride is 

The correct answer is
I > II > III

The relative rate of esterification of compounds I, II, and III with p-nitrobenzoyl chloride depends on steric and electronic factors affecting the reaction at the hydroxyl group.

  1. Structure Analysis:
    • I: The hydroxyl group is on a primary carbon, which usually has less steric hindrance, allowing for a faster esterification rate.
    • II: The hydroxyl group is on a secondary carbon. The increased steric hindrance compared to a primary carbon slows down the esterification rate.
    • III: The hydroxyl group is on a secondary carbon like II, but additional steric factors can further hinder the reaction.
  2. Steric Hindrance and Reactivity:
    • Primary carbons (as in I) have less steric hindrance than secondary carbons, leading to faster reactions.
    • Among secondary carbons, further branching or substituents around the reactive site (as potentially seen in III) can decrease reactivity due to increased steric bulk.
  3. Conclusion: Based on the steric effects and the structure of the compounds, the correct order of reactivity for esterification is I > II > III, as proposed by the correct answer.

Thus, the correct answer is I > II > III.

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Important Questions from Organic Reaction Mechanisms

  1. The Hammett plot for the following transformation is :

  2. The correct sequence of processes involved in the following transformation is :

  3. The relative order of rate constants in the following transformations are

  4. The correct order of basicity for the following compounds is

  5. The intermediates involved in the following reaction are

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