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

Thiol Reactions

Organic Chemistry

12. Alcohols, Ethers, Epoxides and Thiols

Thiol Reactions

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2:40 minutes

Problem 50b

Textbook Question

Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?
b.

Verified step by step guidance

Step 1: Identify the target thioether structure. The given structure contains a sulfur atom bonded to a methyl group and a tert-butyl group. This indicates that the starting materials should include a thiol (R-SH) and an alkyl halide (R-X) that can form these groups.

Step 2: Select the thiol starting material. To introduce the methyl group bonded to sulfur, use methanethiol (CH₃SH) as the thiol starting material.

Step 3: Select the alkyl halide starting material. To introduce the tert-butyl group bonded to sulfur, use tert-butyl bromide (C(CH₃)₃Br) as the alkyl halide starting material.

Step 4: Perform the nucleophilic substitution reaction. The thiol (CH₃SH) acts as a nucleophile and attacks the alkyl halide (C(CH₃)₃Br) in an SN2 reaction mechanism, displacing the bromide ion and forming the thioether product.

Step 5: Ensure reaction conditions are suitable. Use a polar aprotic solvent (e.g., acetone or DMSO) to facilitate the SN2 reaction and maintain mild conditions to avoid side reactions.

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Key Concepts

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

Alkyl Halides

Alkyl halides are organic compounds containing a carbon atom bonded to a halogen atom (such as chlorine, bromine, or iodine). They are key reactants in nucleophilic substitution reactions, where the halogen can be replaced by a nucleophile, such as a thiol, to form new compounds. Understanding the reactivity and structure of alkyl halides is essential for predicting the outcomes of reactions involving these molecules.

Thiol

Thiol compounds, also known as mercaptans, are characterized by the presence of a sulfhydryl group (-SH) attached to a carbon atom. They are nucleophilic in nature, meaning they can donate a pair of electrons to form a bond with electrophiles, such as alkyl halides. This property makes thiols valuable in the synthesis of thioethers through nucleophilic substitution reactions.

Thioether Formation

Thioethers are organic compounds formed by the reaction of an alkyl halide with a thiol, resulting in the substitution of the halogen atom with the thiol's sulfur atom. This reaction typically occurs via an SN2 mechanism, where the nucleophile (thiol) attacks the electrophilic carbon of the alkyl halide, leading to the formation of a thioether and the release of a halide ion. Understanding this mechanism is crucial for successfully synthesizing thioethers.

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Related Practice

Textbook Question

Thiols can be prepared from the reaction of thiourea with an alkyl halide, followed by hydroxide-ion-promoted hydrolysis.

a. Propose a mechanism for the reaction.

Textbook Question

Thiols can be prepared from the reaction of thiourea with an alkyl halide, followed by hydroxide-ion-promoted hydrolysis.

b. What thiol will be formed if the alkyl halide employed is pentyl bromide?

Textbook Question

Dithiothreitol reacts with disulfide bridges in the same way that 2-mercaptoethanol does. With dithiothreitol, however, the equilibrium lies much more to the right. Explain.

Textbook Question

Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?

Textbook Question

(a) Show how you would synthesize the pure (R) enantiomer of 2-butyl methyl sulfide, starting with pure (R)-butan-2-ol and any reagents you need

(b) Show how you would synthesize the pure (S) enantiomer of the product, still starting with (R)-butan-2-ol and any reagents you need.

Textbook Question

Show how you would synthesize the following:

e. cis-pent-2-en-1-thiol from a suitable alkenyl halide

Textbook Question

Predict the product for each of the following reactions.

(c)

Textbook Question

Authentic skunk spray has become valuable for use in scent-masking products. Show how you would synthesize the major component of skunk spray (3-methylbutane-1-thiol and but-2-ene-1-thiol) from any of the readily available butene or from buta-1,3-diene.

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Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?b.

Key Concepts

Alkyl Halides

Thiol

Thioether Formation

Watch next

Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?
b.