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

31. Catalysis in Organic Reactions

Nucleophilic Catalysis

Organic Chemistry

31. Catalysis in Organic Reactions

Nucleophilic Catalysis

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Multiple Choice

Using 3-methyl-1-butene as a starting material, predict the final product based on the list of reagents given?

Product structure of 3-methyl-1-butene with an ethoxy group (OEt) attached.

Product structure of 3-methyl-1-butene with an ethoxy group (EtO) attached.

Product structure of 3-methyl-1-butene with an ethoxy group (OEt) attached, different orientation.

Product structure of 3-methyl-1-butene with an ethoxy group (OEt) attached, same as previous.

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Verified step by step guidance

Begin with the starting material, 3-methyl-1-butene, which is an alkene. The first reagent, HBr in the presence of a peroxide (ROOR), will add across the double bond via a radical mechanism.

In the presence of peroxides, HBr adds to the alkene in an anti-Markovnikov fashion. This means the bromine atom will attach to the less substituted carbon of the double bond, resulting in 1-bromo-3-methylbutane.

Next, the reaction with NaI will involve a nucleophilic substitution. Iodide (I-) is a good nucleophile and will replace the bromine atom in 1-bromo-3-methylbutane, forming 1-iodo-3-methylbutane.

The final step involves the use of KOEt, which is potassium ethoxide. This reagent can act as a base to perform an elimination reaction, specifically an E2 elimination, to form an alkene.

The E2 elimination will result in the formation of an alkene, and the ethoxide ion (EtO-) can also act as a nucleophile to perform a nucleophilic substitution, leading to the formation of an ether. The final product will be an ether with the ethoxy group (OEt) attached to the carbon chain.