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

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions Summary

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Leaving Group Conversions Summary

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Problem 3

Textbook Question

Suggest a reagent for the transformation of a 1° alcohol to a 1° alkyl halide.

Verified step by step guidance

Identify the starting material and the desired product. The starting material is a primary alcohol, and the desired product is a primary alkyl bromide.

Recognize that the transformation involves replacing the hydroxyl group (-OH) of the alcohol with a bromine atom (Br).

Consider common reagents used for converting primary alcohols to primary alkyl halides. One effective reagent for this transformation is phosphorus tribromide (PBr₃).

Understand the mechanism: PBr₃ reacts with the alcohol to form an intermediate, which then undergoes a substitution reaction to replace the -OH group with a bromine atom.

Note that this reaction typically proceeds with inversion of configuration at the carbon center, which is important if the starting alcohol is chiral.

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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 are organic compounds containing a hydroxyl (-OH) group. The reactivity of alcohols varies based on their structure (primary, secondary, or tertiary) and the conditions under which they are transformed. Primary alcohols, like the one in the question, can undergo nucleophilic substitution reactions to form alkyl halides.

Nucleophilic Substitution Reactions

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. For converting a primary alcohol to an alkyl halide, reagents like thionyl chloride (SOCl2) or phosphorus tribromide (PBr3) can be used, facilitating the substitution of the hydroxyl group with a halide.

Reagents for Alcohol Conversion

Specific reagents are required to convert alcohols into alkyl halides effectively. Thionyl chloride and phosphorus tribromide are common choices for this transformation, as they promote the conversion through mechanisms that involve the formation of an intermediate that can easily lose the hydroxyl group and replace it with a halide.

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Related Practice

Textbook Question

Give the structures of the products you would expect when each alcohol reacts with (1) HCl, ZnCl₂; (2) HBr; (3) PBr₃; (4) P/I₂; and (5) SOCl₂.

(a) butan-1-ol

(b) 2-methylbutan-2-ol

Textbook Question

In each case, show how you would synthesize the chloride, bromide, and iodide from the corresponding alcohol.

(a) 1-halobutane (halo = chloro, bromo, iodo)

(b) halocyclopentane

Textbook Question

A graduate student attempted the following reaction and did not isolate the expected product.

(a) What product did they isolate?

(b) What reagent should they have used instead to get their desired product?

Textbook Question

Suggest the appropriate reagents to carry out the following transformations.

(f)

Textbook Question

Suggest the appropriate reagents to carry out the following transformations.

(e)

Textbook Question

Using cyclohexanone as the starting material, describe how each of the following compounds can be synthesized:

Textbook Question

Both cis- and trans-2-methylcyclohexanol undergo dehydration in warm sulfuric acid to give 1-methylcyclohexene as the major alkene product. These alcohols can also be converted to alkenes by tosylation using TsCl and pyridine, followed by elimination using KOC(CH₃)₃ as a strong base. Under these basic conditions, the tosylate of cis-2-methylcyclohexanol eliminates to give mostly 1-methylcyclohexene, but the tosylate of trans-2-methylcyclohexanol eliminates to give only 3-methylcyclohexene. Explain how this stereochemical difference in reactants controls a regiochemical difference in the products of the basic elimination, but not in the acid-catalyzed elimination.

Textbook Question

Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents.

(d) concentrated HBr

(e) TsCl/pyridine, then NaBr

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