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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4:35 minutes

Problem 15a,b

Textbook Question

Use curved arrows to show the movement of electrons in the following reaction steps
a.
b.

Verified step by step guidance

Step 1: Analyze reaction A. The reaction involves formic acid (HCOOH) and hydronium ion (H₃O⁺). The hydronium ion acts as an acid, donating a proton (H⁺) to the oxygen atom of the carbonyl group in formic acid. Use a curved arrow to show the movement of electrons from the lone pair on the oxygen atom of the carbonyl group to the hydrogen atom of H₃O⁺.

Step 2: After the proton transfer in reaction A, the oxygen atom in the carbonyl group becomes positively charged. The hydronium ion loses a proton and forms water (H₂O). Use a curved arrow to show the breaking of the O-H bond in H₃O⁺, with the electrons moving to the oxygen atom.

Step 3: Analyze reaction B. The reaction involves cyclopentene and bromonium ion (Br⁺). The double bond in cyclopentene acts as a nucleophile, attacking the positively charged bromonium ion. Use a curved arrow to show the movement of electrons from the π-bond of the double bond to the bromonium ion.

Step 4: After the attack in reaction B, the bromonium ion forms a bond with one of the carbon atoms in the double bond, creating a carbocation intermediate. Use a curved arrow to show the formation of the new C-Br bond.

Step 5: The bromonium ion stabilizes the carbocation intermediate by donating a lone pair of electrons to the positively charged carbon atom. Use a curved arrow to show the movement of electrons from the bromonium ion to the carbocation, completing the reaction.

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Key Concepts

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

Curved Arrows in Mechanisms

Curved arrows are used in organic chemistry to represent the movement of electrons during chemical reactions. The tail of the arrow indicates the electron source, while the head points to the electron destination. This notation helps visualize how bonds are formed and broken, providing insight into the reaction mechanism.

Acid-Base Reactions

Acid-base reactions involve the transfer of protons (H+) between reactants. In these reactions, acids donate protons, while bases accept them. Understanding the role of acids and bases is crucial for predicting the products of reactions and for drawing accurate reaction mechanisms using curved arrows.

Electrophiles and Nucleophiles

Electrophiles are electron-deficient species that seek electrons, while nucleophiles are electron-rich species that donate electrons. In the context of the provided reactions, identifying these species is essential for understanding how they interact and the direction of electron flow, which is illustrated by the curved arrows in the reaction mechanisms.

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Related Practice

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.

Textbook Question

We discuss the following reactions in subsequent chapters. Given the mechanisms shown, draw the mechanism of the reverse reaction.

(a)

Textbook Question

We discuss the following reactions in subsequent chapters. Given the mechanisms shown, draw the mechanism of the reverse reaction.

(b)

Textbook Question

Use curved arrows to show the flow of electrons that occurs in each step of the following mechanism

Textbook Question

Identify the electrophile and the nucleophile in each of the following reaction steps. Then draw curved arrows to illustrate the bond-making and bond-breaking processes.

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Use curved arrows to show the movement of electrons in the following reaction stepsa. b.

Key Concepts

Curved Arrows in Mechanisms

Acid-Base Reactions

Electrophiles and Nucleophiles

Watch next

Use curved arrows to show the movement of electrons in the following reaction steps
a.
b.