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

4:40 minutes

Problem 6c

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the starting material. The given compound is a cyclohexanol derivative with a tertiary alcohol group attached to the cyclohexane ring. The reaction involves HCl, which suggests an acid-catalyzed substitution reaction.

Step 2: Understand the mechanism. In the presence of HCl, the hydroxyl group (-OH) will be protonated to form water (H2O), which is a good leaving group. This step facilitates the formation of a carbocation intermediate.

Step 3: Consider carbocation stability. The carbocation formed after the departure of water will be a tertiary carbocation, which is highly stable due to hyperconjugation and inductive effects from the adjacent alkyl groups.

Step 4: Predict the nucleophilic attack. The chloride ion (Cl⁻) from HCl will act as a nucleophile and attack the carbocation, leading to the formation of the major product.

Step 5: Conclude the major product. The major product will be a tertiary alkyl chloride, where the hydroxyl group is replaced by a chlorine atom at the same position.

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.

Acid-Base Reactions

In organic chemistry, acid-base reactions involve the transfer of protons (H+) between molecules. In this case, HCl acts as a strong acid, donating a proton to the hydroxyl group (-OH) of cyclohexanol, which leads to the formation of a better leaving group, water. Understanding this concept is crucial for predicting the outcome of reactions involving alcohols and acids.

Carbocation Stability

The formation of carbocations is a key step in many organic reactions, including the reaction of alcohols with acids. The stability of the carbocation intermediate influences the major product formed. Tertiary carbocations are more stable than secondary or primary ones, so the reaction pathway will favor the formation of the most stable carbocation, which ultimately determines the major product.

Nucleophilic Substitution

Nucleophilic substitution reactions involve the replacement of a leaving group by a nucleophile. In the context of the reaction shown, after protonation of the alcohol, the resulting water molecule leaves, allowing a nucleophile (like chloride ion from HCl) to attack the carbocation. This process is essential for understanding how the final product is formed from the initial reactants.

Watch next

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

Start learning