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Ch. 22 - Condensations and Alpha Substitutions of Carbonyl Compounds
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 22 - Condensations and Alpha Substitutions of Carbonyl CompoundsProblem 61(1)
Chapter 22, Problem 61(1)

1. Rank the following compounds in order of increasing acidity.

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1
Identify the functional groups present in each compound. Functional groups such as carboxylic acids, phenols, alcohols, and amines significantly influence acidity.
Analyze the stability of the conjugate base formed after deprotonation of each compound. A more stable conjugate base corresponds to a stronger acid.
Consider the effects of resonance stabilization. If the conjugate base can delocalize its negative charge through resonance, the compound will be more acidic.
Evaluate the inductive effects of electronegative atoms or groups. Electronegative substituents near the acidic proton can stabilize the conjugate base through electron withdrawal, increasing acidity.
Rank the compounds based on the combined effects of resonance, inductive effects, and the inherent acidity of the functional groups. Start with the least acidic compound and progress to the most acidic.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Acidity and pKa

Acidity refers to the tendency of a compound to donate protons (H+) in a solution. The strength of an acid is often measured using the pKa value, where lower pKa values indicate stronger acids. Understanding the relationship between acidity and pKa is crucial for ranking compounds based on their acidic strength.
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Identifying pKa values

Resonance Stabilization

Resonance stabilization occurs when a molecule can be represented by multiple valid Lewis structures, allowing for the delocalization of electrons. This delocalization can stabilize the conjugate base formed after deprotonation, thereby increasing the acidity of the original compound. Recognizing resonance structures is essential for predicting acidity trends.
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Inductive Effect

The inductive effect refers to the electron-withdrawing or electron-donating influence of substituents on a molecule. Electronegative atoms or groups can stabilize the negative charge on a conjugate base through inductive withdrawal, enhancing acidity. Understanding how different substituents affect acidity through this effect is key to ranking compounds.
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Related Practice
Textbook Question

For each molecule shown below,

1. indicate the most acidic hydrogens.

2. draw the important resonance contributors of the anion that results from removal of the most acidic hydrogen.

(h)

2
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Textbook Question

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(a)

1
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Textbook Question

2. Indicate which compounds would be more than 99% deprotonated by a solution of sodium ethoxide in ethanol.

3
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Textbook Question

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(b)

1
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Textbook Question

For each molecule shown below,

1. indicate the most acidic hydrogens.

2. draw the important resonance contributors of the anion that results from removal of the most acidic hydrogen.

(g)

1
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Textbook Question

Predict the products of the following aldol condensations. Show the products both before and after dehydration.

(c)

1
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