
Concept explainers
(a)
Interpretation:
The pKa value for a protonated
Concept introduction:
The stability of a charged species depends on the groups attached to the positively charged atom. The electron withdrawing group increases the concentration of positive charge on the nearby atom. While, the electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge.
(b)
Interpretation:
The pKa value for a protonated amine (R3NH+) depends on the number of alkyl groups attached to N, as shown below. This order disagrees with what we would predict using charge stability. The reason for the discrepancy is to be explained.
Concept introduction:
The stability of a charged species decreases as the effective electronegativity of an atom bearing a positive charge increases. The electron donating group decreases the concentration of positive charge on the nearby atom. This increases the stability of nearby positively charged atom. In general, cations are stabilized by electron-donating groups near the positive charge. Bulky group around the cation, reduces the solvation process. This decreases the stability of the ion and increases acidity.

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Chapter 6 Solutions
Organic Chemistry: Principles And Mechanisms
- What is the name of the following compound? SiMe3arrow_forwardK Draw the starting structure that would lead to the major product shown under the provided conditions. Drawing 1. NaNH2 2. PhCH2Br 4 57°F Sunny Q Searcharrow_forward7 Draw the starting alkyl bromide that would produce this alkyne under these conditions. F Drawing 1. NaNH2, A 2. H3O+ £ 4 Temps to rise Tomorrow Q Search H2arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

