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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2:04 minutes

Problem 51c

Textbook Question

In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.
c.

Verified step by step guidance

Identify the reactants: In the given reaction, the reactants are acetaldehyde (CH₃CHO) and hydrochloric acid (HCl).

Determine the Lewis acid and Lewis base: Acetaldehyde has a carbonyl group (C=O) where the oxygen atom has lone pairs of electrons, making it a Lewis base (nucleophile). HCl can donate a proton (H⁺), making it a Lewis acid (electrophile).

Draw the curved arrows: The lone pair of electrons on the oxygen atom of acetaldehyde will attack the hydrogen atom of HCl, forming a bond between oxygen and hydrogen. This is shown with a curved arrow from the lone pair on oxygen to the hydrogen atom.

Show the movement of electrons: As the bond between H and Cl breaks, the electrons from the H-Cl bond move to the chlorine atom, forming Cl⁻. This is represented by a curved arrow from the H-Cl bond to the chlorine atom.

Draw nonbonding electrons: After the reaction, the oxygen atom in the product has a positive charge due to the formation of the O-H bond, and the chlorine atom has a negative charge due to the gain of electrons, forming Cl⁻. Ensure to show these charges and any nonbonding electrons involved in the process.

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Key Concepts

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

Lewis Acids and Bases

Lewis acids are species that accept electron pairs, while Lewis bases donate electron pairs. In the given reaction, HCl acts as a Lewis acid because it accepts an electron pair from the oxygen atom of the aldehyde, which acts as a Lewis base. Understanding these roles is crucial for identifying the movement of electrons in the reaction.

Curved Arrow Notation

Curved arrows are used in organic chemistry to depict the movement of electron pairs during chemical reactions. In this reaction, a curved arrow would show the electron pair from the oxygen atom moving towards the hydrogen atom of HCl, indicating the formation of a new bond. This notation helps visualize the electron flow and the transformation of reactants to products.

Nonbonding Electrons

Nonbonding electrons, or lone pairs, are valence electrons not involved in bonding. In the reaction, the lone pair on the oxygen atom of the aldehyde is crucial as it participates in forming a bond with the hydrogen from HCl. Recognizing the role of nonbonding electrons is essential for understanding how they influence reactivity and the mechanism of the reaction.

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Related Practice

Textbook Question

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

Textbook Question

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

Textbook Question

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

Textbook Question

Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.

Textbook Question

Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF₃.

(e) CH₃CH₂OH

Textbook Question

Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF₃.

(f) (CH₃)₂S

Textbook Question

Which atoms in the enol ether would you expect to react with Br⁺ ?

Textbook Question

To which atom of formaldehyde would you expect H⁺ to add?

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