The pka values of OH group in 4-cyanophenol and 4-nitrophenol are identical BUT in the di-methylswbstituted compounds C and D differ significantly. The cyano derivative C is more acidic than compound D. Please briefly explain why this is the case (you can use words and drawings). Hint: delocalization... A В OH OH OH OH CN NO2 CN NO2

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterNW4: Nomenclature Worksheet 4: Carbonyl Compounds
Section: Chapter Questions
Problem 31CTQ
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The pka values of OH group in 4-cyanophenol and 4-nitrophenol are identical BUT in
the di-metbylsbstituted compounds C and D differ significantly. The cyano derivative
C is more acidic than compound D. Please briefly explain why this is the case (you can
use words and drawings). Hint: delocalization...
A
B
ОН
OH
OH
ОН
CN
NO2
CN
NO2
Transcribed Image Text:The pka values of OH group in 4-cyanophenol and 4-nitrophenol are identical BUT in the di-metbylsbstituted compounds C and D differ significantly. The cyano derivative C is more acidic than compound D. Please briefly explain why this is the case (you can use words and drawings). Hint: delocalization... A B ОН OH OH ОН CN NO2 CN NO2
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