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

8. Elimination Reactions

Nucleophiles and Basicity

Organic Chemistry

8. Elimination Reactions

Nucleophiles and Basicity

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3:18 minutes

Problem 16

Textbook Question

[FIGURE: KEY MECHANISM 7-1]

Show what happens in step 2 of the example if the solvent acts as a nucleophile (forming a bond to carbon) rather than as a base (removing a proton).

Verified step by step guidance

Step 1: Analyze the given reaction mechanism. In the original step, the solvent (ethanol or methanol) acts as a base, removing a proton from the carbocation intermediate to form a double bond. However, in this modified scenario, the solvent acts as a nucleophile, forming a bond with the carbocation instead.

Step 2: Identify the carbocation intermediate. The positively charged carbon is highly electrophilic and can be attacked by the nucleophilic oxygen atom of the solvent molecule (CH3CH2OH or CH3OH). The lone pair of electrons on the oxygen atom will initiate the attack.

Step 3: Draw the nucleophilic attack. The oxygen atom of the solvent forms a bond with the carbocation, resulting in a new intermediate where the solvent is attached to the carbon. This step involves the movement of electrons from the oxygen's lone pair to the carbocation.

Step 4: Consider the proton transfer. After the nucleophilic attack, the oxygen atom in the solvent will carry a positive charge due to the bond formation. To stabilize this intermediate, a proton transfer occurs, where a nearby base (possibly another solvent molecule) removes a proton from the positively charged oxygen.

Step 5: Finalize the product. The result of this mechanism is a new compound where the solvent is covalently bonded to the original carbon atom. The reaction does not produce a double bond as in the original mechanism but instead forms an ether-like product.

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Key Concepts

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

Nucleophilicity

Nucleophilicity refers to the ability of a species to donate an electron pair to form a new bond. In organic reactions, nucleophiles are typically negatively charged or neutral species with lone pairs of electrons. In the context of the question, the solvent (methanol, CH3OH) acts as a nucleophile, attacking the positively charged carbon center to form a new bond.

Mechanism of Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. The mechanism can proceed via different pathways, such as SN1 or SN2, depending on the structure of the substrate and the conditions. Understanding this mechanism is crucial for predicting the outcome of the reaction when the solvent acts as a nucleophile.

Role of Solvents in Organic Reactions

Solvents can play multiple roles in organic reactions, acting either as a medium for the reaction or participating in the reaction itself. In this case, the solvent (methanol) is not just a passive medium but actively participates as a nucleophile. This dual role can significantly influence the reaction pathway and the products formed, highlighting the importance of solvent choice in organic synthesis.