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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Problem 60e

Textbook Question

Identify the arrows shown by type and predict the product that should result.
(e)

Verified step by step guidance

Step 1: Analyze the reaction mechanism shown in the image. The first arrow indicates the movement of a pair of electrons from the hydroxide ion (HO⁻) to the positively charged carbon atom in the tertiary carbocation. This is a nucleophilic attack, where the hydroxide ion acts as the nucleophile.

Step 2: The second arrow shows the movement of a hydrogen atom (proton transfer) from the hydroxide ion to the adjacent carbon atom. This step stabilizes the intermediate and completes the reaction.

Step 3: Predict the product based on the reaction mechanism. The nucleophilic attack by the hydroxide ion will result in the formation of a new bond between the oxygen atom and the positively charged carbon atom.

Step 4: The proton transfer will result in the removal of one hydrogen atom from the hydroxide ion, converting it into a neutral alcohol group (-OH).

Step 5: The final product will be a tertiary alcohol, where the hydroxyl group (-OH) is attached to the carbon atom that was initially part of the carbocation.

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Key Concepts

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

Reaction Mechanisms

Reaction mechanisms describe the step-by-step process by which reactants transform into products. Understanding the mechanism helps predict the outcome of a reaction, including the types of intermediates formed and the overall energy changes. Key components include nucleophiles, electrophiles, and the role of catalysts.

Arrow Notation in Organic Chemistry

Arrow notation is used to illustrate the movement of electrons during chemical reactions. Curved arrows indicate the flow of electron pairs, showing how bonds are formed or broken. Understanding this notation is crucial for visualizing reaction pathways and predicting products.

Types of Organic Reactions

Organic reactions can be classified into several types, including substitution, addition, elimination, and rearrangement reactions. Each type has distinct characteristics and mechanisms. Recognizing the type of reaction occurring is essential for predicting the products and understanding the underlying chemistry.

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Related Practice

Textbook Question

Identify the arrow types that are shown in each of these arrow-pushing mechanisms.

(iii)

Textbook Question

Acid–base reactions are reversible. Show a mechanism for the reverse of the reactions in Assessment 4.18.

Textbook Question

Identify the nucleophile and the electrophile in each of the following reactions.

(a)

Textbook Question

Show an arrow-pushing mechanism that forms the product on the right from the reactant at left. Two arrows are necessary in each reaction.

(b)

Textbook Question

Identify the arrows shown by type and predict the product that should result.

(a)

Textbook Question

Would you expect the following species to be electrophiles or nucleophiles? Some may be both. Explain your answer.

(e)

Textbook Question

Using curved arrows, show the mechanism of the following reaction:

Textbook Question

For each of the reactions in Problem 15, indicate which reactant is the nucleophile and which is the electrophile.

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Identify the arrows shown by type and predict the product that should result.(e)

Key Concepts

Reaction Mechanisms

Arrow Notation in Organic Chemistry

Types of Organic Reactions

Watch next

Identify the arrows shown by type and predict the product that should result.
(e)