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

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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5:41 minutes

Problem 57a(7)

Textbook Question

a. Show the reagents required to form the primary alcohol in each of the following reactions.

Verified step by step guidance

Step 1: Identify the starting material and the product. The starting material is an epoxide (a three-membered cyclic ether), and the product is a primary alcohol.

Step 2: Recognize the type of reaction. This is a ring-opening reaction of the epoxide to form a primary alcohol. The nucleophile attacks the less substituted carbon of the epoxide due to steric hindrance.

Step 3: Choose the appropriate nucleophile and acidic or basic conditions. To form a primary alcohol, water (H₂O) can act as the nucleophile, and an acid catalyst such as H⁺ (e.g., H₂SO₄) is typically used to protonate the epoxide and facilitate the ring opening.

Step 4: Describe the mechanism. The epoxide is protonated by the acid catalyst, making the oxygen more electrophilic. Water then attacks the less substituted carbon of the epoxide, leading to the formation of the primary alcohol.

Step 5: Summarize the reagents required. The reaction requires water (H₂O) as the nucleophile and an acid catalyst (e.g., H₂SO₄) to form the primary alcohol from the epoxide.

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Key Concepts

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

Epoxide Chemistry

Epoxides are three-membered cyclic ethers that are highly reactive due to the strain in their ring structure. They can undergo ring-opening reactions in the presence of nucleophiles, leading to the formation of various products, including alcohols. Understanding the mechanism of epoxide ring-opening is crucial for predicting the outcome of reactions involving these compounds.

Nucleophilic Attack

Nucleophilic attack is a fundamental concept in organic chemistry where a nucleophile, which is an electron-rich species, attacks an electron-deficient center, such as a carbon atom in an epoxide. This process often leads to the formation of new bonds and is essential for converting epoxides into alcohols. The regioselectivity of the attack can influence the final product's structure.

Reagents for Alcohol Formation

To convert an epoxide into a primary alcohol, specific reagents are required. Typically, a nucleophile such as water or an alcohol is used in the presence of an acid catalyst to facilitate the ring-opening. The choice of nucleophile and conditions can determine whether the resulting alcohol is primary, secondary, or tertiary, making it important to select the appropriate reagents for the desired outcome.

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Related Practice

Textbook Question

How can the following compounds be prepared from the given starting materials?

Textbook Question

Show how each of the following compounds can be prepared, using the given starting material:

Textbook Question

Identify A through O:

Textbook Question

a. Show the reagents required to form the primary alcohol in each of the following reactions.

Textbook Question

Show how you would accomplish the following syntheses. You may use whatever additional reagents you need.

(c)

Textbook Question

Predict the major products of the following reactions.

(d)

Textbook Question

Two of the methods for converting alkyl halides to carboxylic acids are covered in Sections 20-8B and 20-8C. One is formation of a Grignard reagent followed by addition of carbon dioxide and then dilute acid. The other is substitution by cyanide ion, followed by hydrolysis of the resulting nitrile. For each of the following conversions, decide whether either or both of these methods would work, and explain why. Show the reactions you would use.

(a)

(b)

Textbook Question

Predict the products of the following reactions.

(a) sec-butylmagnesium iodide + D₂O

(b) n-butyllithium + CH₃CH₂OH

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