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

3:46 minutes

Problem 6d

Textbook Question

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

Verified step by step guidance

Step 1: Analyze the starting material. The given compound is a cyclopentanol, which contains a hydroxyl (-OH) group attached to a cyclopentane ring. The reaction involves HCl, a strong acid.

Step 2: Understand the reaction mechanism. When alcohols react with HCl, the hydroxyl group is protonated by HCl, forming water as a leaving group. This step increases the electrophilicity of the carbon attached to the hydroxyl group.

Step 3: Consider the formation of a carbocation intermediate. After the water leaves, a carbocation is formed at the carbon where the hydroxyl group was attached. Evaluate the stability of the carbocation. In this case, the carbocation is secondary, which is relatively stable.

Step 4: Predict the nucleophilic attack. The chloride ion (Cl⁻) from HCl will act as a nucleophile and attack the carbocation, forming a new C-Cl bond.

Step 5: Determine the major product. The major product will be the cyclopentane ring with a chlorine atom attached to the carbon where the hydroxyl group was originally located.

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.

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, resulting in the formation of a more saturated product. In the context of the given reaction, HCl acts as the electrophile, adding across the double bond of the cyclic compound, which contains an alcohol group. Understanding this mechanism is crucial for predicting the major product formed.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX (where X is a halogen) to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the regioselectivity of the reaction, guiding us to determine which carbon will bond with the chlorine from HCl in the reaction shown, leading to the major product.

Rearrangement of Carbocations

Carbocation rearrangement is a process where a carbocation (positively charged carbon species) can shift its structure to form a more stable carbocation during a reaction. In the reaction depicted, if a carbocation intermediate is formed, it may rearrange to a more stable form before the final product is produced. Recognizing the potential for rearrangement is essential for accurately predicting the major product of the reaction.

Watch next

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

Start learning