Organic Chemistry (6th Edition)
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 21.3, Problem 7P
Interpretation Introduction

Interpretation: The increasing order of acidity for the labeled CH2 protons is to be shown.

Concept Introduction: The most acidic hydrogen (H) atom or proton is the one which can be easily eliminated from the molecule. In case of carbonyl group, the CH bond that is present on the αcarbon atom of carbonyl group is highly acidic as compared to sp3 hybridized carbon-hydrogen bonds due to the formation of resonance stabilized enolate.

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Rank the indicated a-H’s from most to least acidic (most acidic= 1). Be sure to explain your rankings for each by drawing significant resonance structures for the conjugate base and commenting on any other factors that contribute to your rankings.
Rank the following compounds in order of increasing acidity (1 = least acidic, 3 = most acidic) and in the space provided use resonance (of the conjugate base) to explain why the compound you have labelled “3” is the most acidic.
Rank the labeled protons (Ha–Hc) in mandelic acid, a naturally occurring carboxylic acid in plums and peaches, in order of increasing acidity. Explain in detail why you chose this order.

Chapter 21 Solutions

Organic Chemistry (6th Edition)

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