Organic Chemistry – Some Basic Principles and Techniques

Question

With the help of inductive effect, show that monochloroacetic acid is stronger acid than acetic acid.

Answer


This is because chlorine is an electron withdrawing group (-I effect). It withdraws electrons from the carbon chain towards itself. As a result, electron density on the oxygen atoms of O- H bond decreases. This helps in the release of H+ ions and hence acid strength increases. On the other hand, in the case of acetic acid, a methyl group is an electron releasing group (+ I effect). It displaces the electron towards the carbon chain. As a result, electron density on the oxygen atom of O – H bond increases. Therefore, the release of H+ ions become difficult, so acidic character decreases. Hence chloroacetic acid is a stronger acid than acetic acid.

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