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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2:28 minutes

Problem 49a

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)

Verified step by step guidance

Step 1: Begin by identifying all pushable pairs in the molecule. Pushable pairs include lone pairs of electrons, π-bonds (double or triple bonds), and negative charges. Carefully examine the structure of the molecule to locate these electron sources.

Step 2: Identify all places where electrons can be pushed. These include atoms with positive charges, electron-deficient atoms (such as carbocations), and atoms that can accept electrons due to their electronegativity or hybridization. Look for regions in the molecule where electron movement can stabilize the structure.

Step 3: Apply the rules of resonance to determine valid electron movement. Electrons can be pushed from pushable pairs to electron-accepting regions, ensuring that the resulting resonance structure adheres to the octet rule and does not violate fundamental chemical principles.

Step 4: Draw one valid resonance structure based on the electron movement identified in the previous step. Ensure that the new structure maintains the correct formal charges and connectivity of atoms.

Step 5: Verify the resonance structure by checking that it is a valid representation of the molecule. Confirm that all atoms have appropriate formal charges, the octet rule is satisfied where applicable, and the structure is consistent with the original molecule.

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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. Understanding resonance is crucial for predicting the reactivity and properties of organic compounds.

Electron Pushing (Curved Arrows)

Electron pushing is a method used in organic chemistry to show the movement of electrons during chemical reactions and resonance. Curved arrows are drawn from electron-rich areas (nucleophiles) to electron-poor areas (electrophiles) to indicate the flow of electron density. Mastery of this technique is essential for visualizing reaction mechanisms and understanding how molecular structures change.

Pushable Pairs

Pushable pairs refer to pairs of electrons that can be moved in resonance structures or during reactions. These include lone pairs and pi bonds that can be shifted to form new bonds or to stabilize charges. Identifying pushable pairs is vital for constructing valid resonance structures and predicting the behavior of molecules in various chemical contexts.

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Related Practice

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.

(e)

Textbook Question

Each pair of structures represents two valid resonance structures. Use the arrow-pushing formalism to justify the formation of the one on the left from the one on the right.

(a)

Textbook Question

Each pair of structures represents two valid resonance structures. Use the arrow-pushing formalism to justify the formation of the one on the left from the one on the right.

(b)

Textbook Question

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

(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.

(d)

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)

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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)

Key Concepts

Resonance Structures

Electron Pushing (Curved Arrows)

Pushable Pairs

Watch next

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)