Q97 · CSIR-NET Chemistry, December 2019

Paper: CSIR-NET December 2019 · Subject: Organic Chemistry · Chapter: Organic Spectroscopy · Topic: IR · Marks: 2 · Difficulty: Hard

In IR spectrum, recorded neat, a compound shows a strong and broad band at $3300\,\mathrm{cm^{-1}}$. The band becomes sharp and shifts to $3600\,\mathrm{cm^{-1}}$ when the spectrum is recorded in $\mathrm{CCl_4}$ at high dilution. This proves that the compound has
(a)OH group, which is involved in intra-molecular H-bonding
(b)OH group, which is involved in inter-molecular H-bonding
(c)A terminal alkyne group
(d)OH group, present in severely sterically hindered environment
Answer
Answer: B ✓ checked by 4AB · confidence high
Explanation
A broad 3300 cm⁻¹ band that sharpens and moves to 3600 cm⁻¹ on dilution shows an O–H whose hydrogen bonds are broken by dilution — intermolecular H-bonding (an intramolecular bond would survive dilution).

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