Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene

Bruice8th EditionOrganic ChemistryISBN: 9780135213711당신이 사용하는 게 아니라요?교과서 변경

Bruice 8th Edition

Ch. 8 - Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction • Aromaticity and Electronic Effects: An Introduction to the Reactions of Benzene

문제 6c

8장, 문제 6c

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid.
c.

검증된 단계별 안내

Identify the species in question and determine if it has resonance structures. Resonance occurs when there are delocalized electrons, such as lone pairs, π-bonds, or charges, that can be redistributed across the molecule.

Draw all possible resonance contributors for the species. To do this, move electrons (using curved arrows) while ensuring that the octet rule is satisfied for second-row elements and that formal charges are minimized. Use MathML to represent the structures if needed.

Evaluate the stability of each resonance contributor. Contributors with a full octet on all atoms, minimal formal charges, and negative charges on more electronegative atoms are more stable and contribute more to the resonance hybrid.

Rank the resonance contributors in order of decreasing contribution to the resonance hybrid based on their stability. The most stable contributor will have the highest contribution, while less stable contributors will contribute less.

Draw the resonance hybrid by combining the resonance contributors. Use dashed lines to represent delocalized π-bonds and partial charges to indicate the distribution of charge across the molecule.

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주요 개념

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Resonance Structures

Resonance structures are different Lewis structures for the same molecule that depict the same arrangement of atoms but differ in the placement of electrons. These structures help illustrate the delocalization of electrons within a molecule, which contributes to its stability. The actual structure of the molecule is a resonance hybrid, a weighted average of all valid resonance forms.

Resonance Hybrid

The resonance hybrid is the most stable representation of a molecule, combining the characteristics of all its resonance structures. It reflects the delocalization of electrons, resulting in bond lengths and angles that are intermediate between those predicted by individual resonance forms. The hybrid is often depicted with dashed lines to indicate partial bonds and charges.

Contribution to Resonance Hybrid

The contribution of each resonance structure to the resonance hybrid is determined by factors such as the stability of the structure, the octet rule, and the presence of formal charges. Structures that minimize formal charges and maintain full octets for all atoms are generally more significant contributors. Ranking these structures helps predict the overall electron distribution in the molecule.

Draw resonance contributors for each of the following species and rank them in order of decreasing contribution to the resonance hybrid. Then draw the resonance hybrid. c.