Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter4: Polar Bonds, Polar Reactions
Section: Chapter Questions
Problem 22CTQ
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Question
Would the carboxyl group make the 3rd option the most acidic? Or would the fluorines make the 5th one the most acidic?
Expert Solution
Step 1: Difference in the acidity of aliphatic and aromatic alcohols.
The alcohols in which benzene ring is directly attached to the alcoholic functional group is more acidic than the aliphatic alcohols because phenoxide ion formed by the removal of a hydrogen ion is resonance stabilized due to which the tendency to donate a hydrogen ion increases.
Hence, the alcohols given in the option (A) and (E) will be less acidic than the rest ones. But the alcohol (E) is more acidic than the alcohol (A) because of the -I effect of fluoride groups in the alcohol (E) which is absent in the alcohol (A).
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