Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 2.3, Problem 2.15E
Interpretation Introduction

Interpretation: The site of protonation of acetic acid should be accounted.

Concept introduction: The same molecule that shows characteristics of acid under some certain conditions can also behave as base under some different conditions. For instance, the acetic acid in presence of water loses its proton to water and form H3O+ . Hence it shows acidic behavior in water solvent. However, with stronger acids such as hydrobromic acid the same acetic acid accepts proton through the carbonyl oxygen.

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Let's say we had an acid-base reaction of acetic acid and hydronium. What would the products be? Where would the positive charge be for the acetic acid's conjugate acid?  Why would the hydrogen add to the oxygen that is double bonded instead of the oxygen that is single bonded (on acetic acid)?
For the compound below please determine which of the two protons (a) or (b) is more acidic using the ARIO rule and explain your reasoning. Note: To answer the question correctly, please draw both Conjugate Base 1 and Conjugate Base 2. Determine which of the two protons is more acidic using the ARIO rule and explain your reasoning - if the reason is R (number of Resonance Structures) please draw all the resonance structures. Make sure you keep track of all formal charges and lone pairs.
Draw the phosphonium ylide that results when a proton is removed by butyllithium. Be sure to include charges and lone pairs where applicable. Draw the resonance structure of the phosphonium ylide product. Hint: phosphorus may have more than eight valence electrons.
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