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Ch. 15 - Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728당신이 사용하는 게 아니라요?교과서 변경
15장, 문제 27a

Draw the important resonance contributors for the following cations, anions, and radicals.
(a)

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1
Step 1: Identify the structure provided in the image. The molecule contains a carbocation (CH2+) attached to a conjugated system of double bonds. This indicates that resonance contributors can be drawn by delocalizing the positive charge across the π-system.
Step 2: Begin by moving the π-electrons from the double bond adjacent to the carbocation towards the carbocation. This creates a new resonance structure where the positive charge is shifted to the carbon atom that was part of the double bond.
Step 3: Continue the resonance process by moving the π-electrons from the next double bond in the conjugated system towards the newly formed carbocation. This results in another resonance structure where the positive charge is further delocalized.
Step 4: Repeat the process for the remaining double bond in the conjugated system, ensuring that the positive charge is distributed across the entire π-system. Each resonance structure should maintain the overall charge and connectivity of the molecule.
Step 5: Verify that all resonance contributors are valid by checking that each structure adheres to the rules of resonance (e.g., no violation of the octet rule, proper placement of charges). Highlight the delocalization of the positive charge as the key stabilizing feature of the molecule.

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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.
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3m

주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

Resonance Structures

Resonance structures are different ways of drawing the same molecule that illustrate the delocalization of electrons. They help in understanding the stability and reactivity of a compound. In resonance, the actual structure is a hybrid of these contributors, which can affect properties like acidity, basicity, and reactivity.
추천 영상:
03:04
Drawing Resonance Structures

Cation Stability

Cation stability refers to the relative stability of positively charged species. Factors influencing cation stability include the degree of alkyl substitution, resonance stabilization, and the electronegativity of adjacent atoms. More stable cations are generally formed from structures that allow for greater electron delocalization.
추천 영상:
가이드 코스
0:52
Cationic Polymerization Concept 3

Electron Delocalization

Electron delocalization occurs when electrons are spread over multiple atoms rather than localized between two. This phenomenon is crucial in resonance structures, as it allows for the stabilization of charged species like cations and anions. Delocalization can lower the energy of a molecule, making it more stable and less reactive.
추천 영상:
03:54
The 18 and 16 Electron Rule