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

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3:36 minutes

Problem 6a

Textbook Question

What is the major product of each of the following reactions?
a.

Verified step by step guidance

Step 1: Identify the type of reaction. The reaction involves an alcohol (OH group) reacting with HCl, which is a strong acid. This is a substitution reaction where the hydroxyl group (-OH) is replaced by a halide (Cl).

Step 2: Determine the mechanism. Since the alcohol is tertiary (the carbon attached to the -OH group is bonded to three other carbons), the reaction will proceed via an SN1 mechanism. This is because tertiary carbons stabilize the carbocation intermediate formed during the reaction.

Step 3: Protonation of the alcohol. The hydroxyl group (-OH) is protonated by HCl, forming water (H2O), which is a good leaving group. This step increases the likelihood of the leaving group departing.

Step 4: Formation of the carbocation. After the water molecule leaves, a tertiary carbocation is formed. This carbocation is highly stable due to hyperconjugation and inductive effects from the surrounding alkyl groups.

Step 5: Nucleophilic attack. The chloride ion (Cl⁻) from HCl acts as a nucleophile and attacks the carbocation, forming the final product, which is a tertiary alkyl chloride.

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Key Concepts

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

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In this case, the hydroxyl group (OH) acts as a nucleophile, and when reacting with HCl, it can be substituted by a chloride ion (Cl-), leading to the formation of an alkyl chloride.

Reactivity of Alcohols

Alcohols are organic compounds containing hydroxyl (-OH) groups, and their reactivity can vary based on the structure of the alcohol. In this reaction, the presence of HCl facilitates the conversion of the alcohol into a more reactive alkyl halide, which is often more favorable for further reactions, such as elimination or substitution.

Mechanism of Reaction

Understanding the mechanism of the reaction is crucial for predicting the major product. The reaction typically proceeds via a two-step mechanism: protonation of the alcohol by HCl to form a better leaving group, followed by the nucleophilic attack by chloride ion, resulting in the formation of the alkyl chloride as the major product.

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