Chemistry - STRUCTURAL ISOMERISM Question with Solution | TestHub

ChemistrySTRUCTURAL ISOMERISMTAUTOMERISMMedium2 minQB
ChemistryMediumsingle choice

Indicate which hydrogen(s) in each of the following molecules (if any) would be exchanged for deuterium following base treatment in D₂O :

structure

Options:

Answer:
C
Solution:

Under OD⁻/D₂O only the alpha C-H protons of the two carbonyls and the O-H proton exchange. The alpha positions are : the CH₂ between the two C=O groups (2H, doubly activated), the outer CH₂ alpha to the upper C=O (2H), and the ring-junction CH alpha to the lower C=O (1H). The O-H proton exchanges instantly. Total : 5 C-H protons + 1 O-H proton = 6 hydrogens exchanged; all other ring hydrogens (not alpha to a carbonyl) stay in place.

Stream:JEESubject:ChemistryTopic:STRUCTURAL ISOMERISMSubtopic:TAUTOMERISM
⏱ 2mℹ️ Source: QB

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