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

3. Acids and Bases

Reaction Mechanism

Organic Chemistry

3. Acids and Bases

Reaction Mechanism

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2:44 minutes

Problem 5i

Textbook Question

Predict the product that results from the following 'pushed electrons.'
(i)

Verified step by step guidance

Step 1: Analyze the given reaction mechanism and identify the 'pushed electrons' in the provided structure. Pushed electrons typically indicate movement of electron density, such as bond formation, bond breaking, or resonance.

Step 2: Determine the type of reaction occurring. For example, is it a nucleophilic substitution, elimination, addition, or rearrangement? This will help predict the product based on the electron movement.

Step 3: Identify the functional groups involved and their reactivity. For instance, if a nucleophile is attacking an electrophile, locate the electrophilic center and predict the bond formation.

Step 4: Use curved arrow notation to track the electron flow. Ensure that all atoms obey the octet rule (or duet rule for hydrogen) and check for charge conservation throughout the mechanism.

Step 5: Draw the resulting product structure based on the electron movement. Confirm that the product is stable and consistent with the reaction mechanism provided.

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Key Concepts

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

Electron Pushing Mechanism

The electron pushing mechanism, often depicted using curved arrows, illustrates the movement of electrons during chemical reactions. This technique helps visualize how nucleophiles donate electrons to electrophiles, facilitating bond formation or breaking. Understanding this mechanism is crucial for predicting reaction products and determining the reaction pathway.

Nucleophiles and Electrophiles

Nucleophiles are species that donate an electron pair to form a chemical bond, while electrophiles are electron-deficient species that accept electron pairs. Recognizing the roles of these species in a reaction is essential for predicting the outcome of electron-pushing scenarios. Their interaction often dictates the direction and type of the resulting product.

Reaction Mechanisms

A reaction mechanism is a step-by-step description of the process by which reactants transform into products. It includes details about the intermediates formed, the transition states, and the energy changes involved. Understanding the mechanism allows chemists to predict products accurately and provides insight into the stability and reactivity of different compounds.

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Related Practice

Textbook Question

The following reaction steps are shown using conventional electron pushing. (b) Use the bouncing arrow formalism to illustrate the formation of only the product shown.

(c)

Textbook Question

Predict the product that results from the following 'pushed electrons.'

(a)

Textbook Question

Predict the product that results from the following 'pushed electrons.'

(c)

Textbook Question

Predict the product that results from the following 'pushed electrons.'

(f)

Textbook Question

The following reaction steps are shown using conventional electron pushing. (a) Draw the second product whose formation would have been rationalized with this same arrow.

(c)

Textbook Question

Why are NH₃ and CH₃NH₂ no longer nucleophiles when they are protonated?

Textbook Question

In each case, circle the stronger nucleophile.

(d)

Textbook Question

We show in Chapter 20 that α , β-unsaturated ketones are electrophilic at C₄. Rationalize this observation.

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