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

10. Addition Reactions

Epoxide Reactions

Organic Chemistry

10. Addition Reactions

Epoxide Reactions

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3:48 minutes

Problem 60c

Textbook Question

What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?
c. 0.1MNaOH

Verified step by step guidance

Identify the structure of 2-ethyloxirane. It is an epoxide (a three-membered cyclic ether) with an ethyl group attached to one of the carbons in the ring.

Understand the reactivity of epoxides in the presence of a base like NaOH. Epoxides are highly strained and reactive, and bases can open the ring via a nucleophilic attack.

Determine the site of nucleophilic attack. In basic conditions, the nucleophile (OH⁻) will attack the less substituted carbon of the epoxide due to steric hindrance and electronic effects.

Write the mechanism for the reaction. The OH⁻ attacks the less substituted carbon of the epoxide, breaking the C-O bond and opening the ring. This results in the formation of a diol (a molecule with two hydroxyl groups).

Assign the stereochemistry of the product. The nucleophilic attack occurs with inversion of configuration at the carbon being attacked, while the other carbon retains its configuration. Ensure the final product reflects this stereochemical outcome.

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Key Concepts

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

Epoxide Reactivity

Epoxides, or oxiranes, are three-membered cyclic ethers that are highly reactive due to the strain in their ring structure. This strain makes them susceptible to nucleophilic attack, which can lead to ring-opening reactions. Understanding how epoxides react with nucleophiles is crucial for predicting the products of reactions involving them.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction mechanism in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the case of epoxides, a nucleophile such as hydroxide ion (OH-) can attack the less hindered carbon atom of the epoxide, leading to the opening of the ring and the formation of an alcohol. This concept is essential for determining the major product of the reaction.

Regioselectivity

Regioselectivity refers to the preference of a chemical reaction to occur at one site over another in a molecule. In the context of epoxide reactions, the regioselectivity is influenced by steric and electronic factors, which dictate which carbon atom in the epoxide is attacked by the nucleophile. Understanding regioselectivity helps in predicting the specific product formed when 2-ethyloxirane reacts with NaOH.

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Textbook Question

The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.

a. What would be the major product if the NIH shift occurs? (Hint: A C—H bond is easier to break than a C—D bond.)

Textbook Question

Draw the mechanism for formation of the two addition products.

Textbook Question

Propose a mechanism for each of the following reactions:

Textbook Question

What is the major product obtained from the reaction of 2-ethyloxirane with each of the following reagents?

d. CH₃OH/CH₃O^-

Textbook Question

Write the appropriate reagent over each arrow.

Textbook Question

Two stereoisomers are obtained from the reaction of cyclopentene oxide and dimethylamine. The R,R-isomer is used in the manufacture of eclanamine, an antidepressant. What other isomer is obtained?

Textbook Question

Predict the product of the following reactions.

(a)

Textbook Question

Predict the major products of the following reactions, including stereochemistry where appropriate.

a. 2,2-dimethylxirane + H⁺/H₂¹⁸O (oxygen labeled water)

b. 2,2-dimethylxirane + H¹⁸O^–/H₂¹⁸O (oxygen labeled water)

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