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

11. Radical Reactions

Radical Reaction

Organic Chemistry

11. Radical Reactions

Radical Reaction

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2:53 minutes

Problem 4d

Textbook Question

Show how you would accomplish the following synthetic conversions.
(d) 2−methylbutan-2-ol → 2-bromo-3-methylbutane

Verified step by step guidance

Step 1: Identify the functional group in the starting material, 2-methylbutan-2-ol. It contains a tertiary alcohol (-OH group attached to a tertiary carbon). This is important because tertiary alcohols undergo substitution reactions readily under acidic conditions.

Step 2: Recognize that the target molecule, 2-bromo-3-methylbutane, requires the replacement of the hydroxyl (-OH) group with a bromine atom (Br). This suggests a substitution reaction mechanism.

Step 3: Select an appropriate reagent for the substitution reaction. Use hydrobromic acid (HBr) as the reagent, as it is commonly used to convert alcohols to alkyl bromides via an SN1 mechanism. The tertiary alcohol will form a stable carbocation intermediate during the reaction.

Step 4: Write the reaction mechanism. The hydroxyl group is protonated by HBr, forming water as a leaving group. This generates a tertiary carbocation intermediate. Bromide ion (Br⁻) then attacks the carbocation, resulting in the formation of 2-bromo-3-methylbutane.

Step 5: Verify the stereochemistry and structure of the product. Since the reaction proceeds via an SN1 mechanism, the product may be racemic if the carbocation intermediate is chiral. However, in this case, the product is achiral, so stereochemistry is not a concern.

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Key Concepts

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

Alcohols and Their Reactivity

Alcohols, such as 2-methylbutan-2-ol, are organic compounds containing a hydroxyl (-OH) group. Their reactivity is influenced by the structure of the alcohol, including whether it is primary, secondary, or tertiary. In this case, 2-methylbutan-2-ol is a tertiary alcohol, which can undergo substitution reactions to form alkyl halides.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group (like -OH in alcohols) with a nucleophile (such as Br-). In the conversion of 2-methylbutan-2-ol to 2-bromo-3-methylbutane, the hydroxyl group is replaced by a bromine atom through an SN1 or SN2 mechanism, depending on the conditions and substrate structure.

Stereochemistry and Isomerism

Stereochemistry refers to the spatial arrangement of atoms in molecules and is crucial in organic synthesis. The conversion from 2-methylbutan-2-ol to 2-bromo-3-methylbutane may lead to different stereoisomers, depending on the reaction pathway. Understanding how to manage stereochemistry is essential for predicting the outcome of synthetic reactions.

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