Organic Chemistry Basics 2 Question 80

80. Explain, why o-hydroxybenzaldehyde is a liquid at room temperature while $p$-hydroxybenzaldehyde is a high melting solid?

(1999)

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Solution:

  1. Intramolecular H-bonding in ortho-hydroxybenzaldehyde decreases its melting point as well as boiling point.

Molecules of p-hydroxybenzaldehyde is symmetrical, associated together by intermolecular H-bonds, has higher boiling point and melting point.

Intramolecular H-bonding