The powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons (i.e., protons attached to a carbon that is adjacent to the carbonyl group). The effect varies depending on what else is attached to the carbonyl, and whether there is a second carbonyl group attached to the a-carbon. Rank the structures from highest acidity (lowest pK, value) to lowest acidity (highest pK, value). The acidic hydrogen is indicated in blue in each structure. Highest acidity Lowest acidity Answer Bank CH CH H3C CH3 H H. H;C H. H CH3 CH3

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 powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons (i.e., protons attached to a
carbon that is adjacent to the carbonyl group). The effect varies depending on what else is attached to the carbonyl, and
whether there is a second carbonyl group attached to the a-carbon.
Rank the structures from highest acidity (lowest pK, value) to lowest acidity (highest pK, value). The acidic hydrogen is
indicated in blue in each structure.
Highest acidity
Lowest acidity
Answer Bank
H;C,
CH,
H-
CH,
CH
H3C
CH3
H
H.
CH3
H3C
H.
CH3
CH3
H
Transcribed Image Text:The powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons (i.e., protons attached to a carbon that is adjacent to the carbonyl group). The effect varies depending on what else is attached to the carbonyl, and whether there is a second carbonyl group attached to the a-carbon. Rank the structures from highest acidity (lowest pK, value) to lowest acidity (highest pK, value). The acidic hydrogen is indicated in blue in each structure. Highest acidity Lowest acidity Answer Bank H;C, CH, H- CH, CH H3C CH3 H H. CH3 H3C H. CH3 CH3 H
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