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

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Alcohol Synthesis

Previous problemNext problem

Problem 15d

Textbook Question

Suggest a reagent and a reactant that could be combined to make each of the following alcohols.
(d)

Verified step by step guidance

Identify the starting material and the product. The starting material is cyclopropyl ethylene, and the product is cyclopropyl ethanol.

Recognize that the transformation involves the addition of an OH group to the terminal carbon of the alkene, indicating a hydration reaction.

Consider the Markovnikov addition of water across the double bond, which typically requires an acid catalyst. A common reagent for this transformation is dilute sulfuric acid (H₂SO₄) or phosphoric acid (H₃PO₄) in the presence of water.

Alternatively, consider using oxymercuration-demercuration, which involves the use of mercuric acetate (Hg(OAc)₂) followed by reduction with sodium borohydride (NaBH₄) to achieve Markovnikov hydration without rearrangement.

Ensure that the chosen method does not lead to rearrangement or side reactions, maintaining the integrity of the cyclopropyl ring structure in the product.

Verified video answer for a similar problem:

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

Play a video:

Was this helpful?

Key Concepts

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

Alcohol Functional Group

Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) groups attached to a carbon atom. Understanding the structure and properties of alcohols is essential for identifying suitable reactants and reagents for their synthesis. The position of the hydroxyl group can significantly influence the reactivity and properties of the alcohol.

Reagents in Organic Synthesis

Reagents are substances that are added to a reaction to cause a chemical change. In the context of alcohol synthesis, common reagents include strong acids, bases, or specific nucleophiles that can facilitate the formation of the alcohol from a precursor. Knowing the appropriate reagents for different types of alcohols, such as primary, secondary, or tertiary, is crucial for successful synthesis.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions are a fundamental type of reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. This concept is particularly relevant when synthesizing alcohols from alkyl halides or other electrophiles. Understanding the mechanisms of these reactions, including SN1 and SN2 pathways, helps in predicting the products and conditions needed for the desired alcohol.

Watch next

Master Forming alcohols through Oxymercuration-Reduction. with a bite sized video explanation from Johnny

Start learning