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

Grignard Reaction

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Grignard Reaction

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3:16 minutes

Problem 8b

Textbook Question

Predict the product of the following epoxide addition reactions.
(b)

Verified step by step guidance

Identify the structure of the epoxide. An epoxide is a three-membered cyclic ether with significant ring strain, making it highly reactive toward nucleophiles.

Determine the reaction conditions. If the reaction occurs under acidic conditions, the epoxide will be protonated first, making it more electrophilic. If the reaction occurs under basic or neutral conditions, the nucleophile will directly attack the less substituted carbon of the epoxide due to steric hindrance.

Analyze the regioselectivity of the reaction. Under acidic conditions, the nucleophile typically attacks the more substituted carbon of the epoxide due to the formation of a more stable carbocation-like intermediate. Under basic conditions, the nucleophile attacks the less substituted carbon due to steric factors.

Consider the stereochemistry of the product. The nucleophilic attack on the epoxide occurs via an SN2 mechanism, leading to an inversion of configuration at the carbon being attacked.

Draw the final product by opening the epoxide ring and attaching the nucleophile to the appropriate carbon based on the reaction conditions and regioselectivity. Ensure the stereochemistry is correctly represented in the product.

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Key Concepts

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

Epoxide Structure

Epoxides are three-membered cyclic ethers characterized by a highly strained ring structure. This strain makes them reactive intermediates in organic reactions, particularly in nucleophilic addition reactions. The oxygen atom in the epoxide contributes to the ring's reactivity, allowing nucleophiles to attack the less hindered carbon atom adjacent to the oxygen.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic center, leading to the formation of a new bond. In the case of epoxides, nucleophiles can open the strained ring by attacking one of the carbon atoms, resulting in the formation of an alcohol or other functional groups depending on the nucleophile used.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to occur at one site over another in a molecule. In epoxide addition reactions, the regioselectivity is influenced by steric and electronic factors, determining which carbon atom the nucleophile will attack. Understanding regioselectivity is crucial for predicting the major product of the reaction.

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Related Practice

Textbook Question

Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.

(b)

Textbook Question

Show how you would synthesize following tertiary alcohol by adding an appropriate Grignard reagent to a ketone.

d. 2-cyclopentylpentan-2-ol

Textbook Question

Point out the flaws in the following incorrect Grignard syntheses.

(c)

(d)

Textbook Question

A variety of organometallics, which as strong nucleophiles can react with epoxides, are introduced in Chapter 16. Predict the product of these reactions. [Hint: Assume the carbon–metal bond in each is ionic, with the carbon possessing the negative charge.]

(b)

Textbook Question

Addition to an epoxide occurs via an S_N2 reaction, but the stereochemistry of the epoxide is retained in the following reaction. Why?

Textbook Question

Show how you would synthesize the following:

f. 2,5-dimethylhexane from a four-carbon alkyl halide

Textbook Question

Predict the products of the following reactions.

(a) allyl bromide + cyclohexyl magnesium bromide

Textbook Question

Show how the reaction of an allylic halide with a Grignard reagent might be used to synthesize the following hydrocarbons.

c. 1-cyclopentylpent-2-ene