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  • Organic Chemistry Resonance

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    Jace Villanueva
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    This document discusses the rules for drawing resonance structures in organic chemistry. It states that resonance only involves lone pairs and pi bonds, not sigma bonds. It provides guidelines for forming pi bonds and lone pairs, including that pi bonds can only be formed with carbocations or atoms losing pi bonds, and lone pairs are only significant when moving electrons toward more electronegative atoms or making room for pi bonds. Electron-pushing arrows must either break or form a bond, as directed. Charges change with each structure, making the initial tail more positive and final head more negative, except in cyclic structures where charges do not change. The overall charge is the same across all resonance structures.

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    This document discusses the rules for drawing resonance structures in organic chemistry. It states that resonance only involves lone pairs and pi bonds, not sigma bonds. It provides guidelines for forming pi bonds and lone pairs, including that pi bonds can only be formed with carbocations or atoms losing pi bonds, and lone pairs are only significant when moving electrons toward more electronegative atoms or making room for pi bonds. Electron-pushing arrows must either break or form a bond, as directed. Charges change with each structure, making the initial tail more positive and final head more negative, except in cyclic structures where charges do not change. The overall charge is the same across all resonance structures.

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    156 views1 page

    Organic Chemistry Resonance

    Uploaded by

    Jace Villanueva
    This document discusses the rules for drawing resonance structures in organic chemistry. It states that resonance only involves lone pairs and pi bonds, not sigma bonds. It provides guidelines for forming pi bonds and lone pairs, including that pi bonds can only be formed with carbocations or atoms losing pi bonds, and lone pairs are only significant when moving electrons toward more electronegative atoms or making room for pi bonds. Electron-pushing arrows must either break or form a bond, as directed. Charges change with each structure, making the initial tail more positive and final head more negative, except in cyclic structures where charges do not change. The overall charge is the same across all resonance structures.

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    Attribution Non-Commercial (BY-NC)
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    organic chemistry RESONANCE STRUCTURES Resonance involves lone pairs and pi bonds only.

    If sigma bonds are involved, then you are dealing with a reaction, not with resonance. rules for drawing resonance structures Forming a pi bond is only legal when it is formed with: (1) a carbocation, or (2) an atom thats simultaneously losing a pi bond.
    (Its also legal to form a pi bond with an atom that can have an expanded octet, but this rarely comes up.)

    lone pair pi bond pi bond pi bond

    pi bond

    lone pair

    Forming a lone pair is only significant when youre: (1) moving electrons toward the more electronegative atom, or (2) making room for a pi bond .

    electron-pushing arrows and the bonds Every electron-pushing arrow tells you to: (1) break a bond, or (2) form a bond, or (3) break a bond and form a bond. You should break or form a bond only if there is specific electron-pushing arrow telling you to do so. electron-pushing arrows and the charges For every new resonance structure, you should change two charges: the atom at the initial tail becomes one step more positive, and the atom at the final head becomes one step more negative. Exception: If the electron-pushing arrows form a cycle, then there is no initial tail or final head, and hence no charges to change. The net charge should be the same for all the resonance structures of a compound.

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