Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

1. A Review of General Chemistry

Resonance Structures

Organic Chemistry

1. A Review of General Chemistry

Resonance Structures

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1:02 minutes

Problem 64d

Textbook Question

Two resonance structures are shown for each molecule. Use the arrow-pushing formalism to represent the electron flow from the structure on the left to the one on the right.
(d)

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Identify the regions in the molecule where electron movement occurs. Look for lone pairs, π-bonds, or formal charges that can participate in resonance.

Determine the direction of electron flow. Resonance structures involve the movement of electrons, typically from a region of high electron density (like a lone pair or π-bond) to a region of lower electron density (like a positive charge or an adjacent π-system).

Use curved arrows to represent the movement of electrons. Each arrow starts at the source of the electrons (e.g., a lone pair or a bond) and points to where the electrons are moving (e.g., another bond or an atom).

Ensure that the octet rule is satisfied for all atoms involved in the resonance structure. Adjust the placement of electrons accordingly to avoid overfilling or underfilling the valence shell of any atom.

Verify that the resulting resonance structure is valid. Check that the formal charges are correctly assigned and that the overall charge of the molecule remains unchanged between the two resonance structures.

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Key Concepts

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

Resonance Structures

Resonance structures are different Lewis structures for the same molecule that depict the same arrangement of atoms but differ in the distribution of electrons. These structures help illustrate the delocalization of electrons within a molecule, which can stabilize it. The actual structure of the molecule is a hybrid of all possible resonance forms, reflecting the true electron density more accurately than any single structure.

Arrow-Pushing Formalism

Arrow-pushing formalism is a method used in organic chemistry to depict the movement of electrons during chemical reactions. Curved arrows indicate the direction of electron flow, with the tail of the arrow showing where the electrons are coming from and the head indicating where they are going. This technique is essential for visualizing mechanisms and understanding how reactants transform into products.

Electron Flow

Electron flow refers to the movement of electrons during chemical reactions, particularly in the context of bond formation and breaking. Understanding electron flow is crucial for predicting the behavior of molecules during reactions, as it determines how bonds are made or broken. In resonance structures, electron flow can illustrate how electrons are delocalized, affecting the stability and reactivity of the molecule.

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Related Practice

Textbook Question

Draw the resonance structure that would result from the indicated movement of electrons.

(a)

Textbook Question

For each of the molecules shown, do the following:

(i) Identify all pushable pairs.

(ii) Identify all places where electrons can be pushed.

(iii) Draw one valid resonance structure.

(a)

Textbook Question

In the following molecules, identify all pushable electron pairs.

(a)

Textbook Question

Two resonance structures are shown for each molecule. Use the arrow-pushing formalism to represent the electron flow from the structure on the left to the one on the right.

(b)

Textbook Question

Two resonance structures are shown for each molecule. Use the arrow-pushing formalism to represent the electron flow from the structure on the left to the one on the right.

(f)

Textbook Question

Identify the resonance structure that will be produced given the molecule shown and the electron flow indicated.

(a)

Textbook Question

Identify the resonance structure that will be produced given the molecule shown and the electron flow indicated.

(c)

Textbook Question

Draw the important resonance forms of the following free radicals.

(c)

(d)

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