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

7. Substitution Reactions

Substitution Comparison

Organic Chemistry

7. Substitution Reactions

Substitution Comparison

Previous problemNext problem

6:25 minutes

Problem 121

Textbook Question

Propose a mechanism for the following reaction:

Verified step by step guidance

Step 1: Analyze the reactants and products. The starting material is a tertiary alkyl chloride, and the product is an ether. The reaction occurs in ethanol (C₂H₅OH), which suggests that ethanol acts as both the solvent and the nucleophile.

Step 2: Recognize the reaction type. This is likely an SN1 reaction because the substrate is a tertiary alkyl chloride, which favors the formation of a stable carbocation intermediate.

Step 3: Initiate the mechanism. The reaction begins with the dissociation of the C-Cl bond in the tertiary alkyl chloride, forming a carbocation intermediate. This step is facilitated by the polar protic solvent ethanol.

Step 4: Nucleophilic attack. The ethanol molecule (C₂H₅OH) acts as the nucleophile and attacks the carbocation, forming a new bond between the oxygen atom of ethanol and the carbon atom of the carbocation.

Step 5: Proton transfer. The positively charged oxygen atom in the intermediate loses a proton (H⁺) to another ethanol molecule or the solvent, resulting in the formation of the ether product.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (like Cl) by a nucleophile (like ethyl alcohol). In this process, the nucleophile donates a pair of electrons to form a new bond, while the leaving group departs with its electrons. Understanding the mechanism, whether it follows an SN1 or SN2 pathway, is crucial for predicting the outcome of the reaction.

Mechanism of SN2 Reactions

In an SN2 reaction, the nucleophile attacks the electrophilic carbon atom from the opposite side of the leaving group, leading to a concerted mechanism where bond formation and bond breaking occur simultaneously. This results in an inversion of configuration at the carbon center. Recognizing the stereochemical implications is important for understanding the product's structure.

Role of Solvents in Organic Reactions

The choice of solvent can significantly influence the rate and outcome of organic reactions. Polar protic solvents can stabilize ions and facilitate SN1 mechanisms, while polar aprotic solvents favor SN2 reactions by enhancing nucleophilicity. In this reaction, the presence of ethyl alcohol as a solvent and nucleophile suggests a potential for an SN2 mechanism, impacting the reaction dynamics.

Watch next

Master How do we predict if the mechanism is SN1 or SN2? with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

For each reaction, give the expected substitution product, and predict whether the mechanism will be predominantly first order (SN1) or second order (SN2).

d. cyclohexylbromide + methanol

e. cyclohexylbromide + sodium ethoxide