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

14. Synthetic Techniques

Moving Functionality

Organic Chemistry

14. Synthetic Techniques

Moving Functionality

Next problem

3:07 minutes

Problem 40d

Textbook Question

Show how you would convert 2-methylcyclopentanol to the following products. Any of these products may be used as the reactant in any subsequent part of this problem.
d. 1-methylcyclopentanol

Verified step by step guidance

Step 1: Recognize that the problem involves a rearrangement of the methyl group from the 2-position to the 1-position on the cyclopentanol ring. This suggests that a carbocation rearrangement might be involved.

Step 2: Begin by protonating the hydroxyl group (-OH) of 2-methylcyclopentanol using an acid catalyst (e.g., H₂SO₄ or H₃PO₄). This converts the hydroxyl group into a better leaving group, forming water (H₂O).

Step 3: Once the hydroxyl group leaves, a carbocation intermediate is formed at the 2-position of the cyclopentane ring. This is a secondary carbocation.

Step 4: A 1,2-hydride shift occurs, where a hydrogen atom from the 1-position migrates to the 2-position. This stabilizes the carbocation by forming a more stable tertiary carbocation at the 1-position.

Step 5: Finally, water (H₂O) or another nucleophile can attack the carbocation at the 1-position, leading to the formation of 1-methylcyclopentanol as the 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.

Alcohols and Their Reactions

Alcohols are organic compounds containing a hydroxyl (-OH) group. They can undergo various reactions, including dehydration, oxidation, and substitution. Understanding the reactivity of alcohols is crucial for converting one alcohol to another, as different reaction pathways can lead to the desired product.

Isomerism in Organic Chemistry

Isomerism refers to the existence of compounds with the same molecular formula but different structural arrangements. In this case, 2-methylcyclopentanol and 1-methylcyclopentanol are structural isomers. Recognizing isomerism is essential for understanding how to manipulate molecular structures to achieve specific transformations.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group by a nucleophile. In the context of alcohols, this can occur through mechanisms such as SN1 or SN2. Knowing how to apply these mechanisms allows for the conversion of one alcohol to another by effectively substituting functional groups.

Watch next

Master Moving Functionality in Synthesis with a bite sized video explanation from Johnny

Start learning