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

Previous problemNext problem

2:11 minutes

Problem 50c,d

Textbook Question

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

Verified step by step guidance

Step 1: Identify the structure of the thioether product. The given thioether has two alkyl groups attached to a sulfur atom. In this case, the alkyl groups are isopropyl groups.

Step 2: Choose the appropriate alkyl halide and thiol starting materials. To form the thioether, you need an alkyl halide with the isopropyl group (e.g., isopropyl bromide or isopropyl chloride) and a thiol with the same isopropyl group (e.g., isopropyl thiol).

Step 3: Plan the reaction mechanism. The reaction involves a nucleophilic substitution (SN2) mechanism where the thiol acts as a nucleophile and attacks the alkyl halide, displacing the halide ion.

Step 4: Write the reaction conditions. Combine the alkyl halide and thiol in the presence of a base (e.g., NaOH or KOH) to deprotonate the thiol, increasing its nucleophilicity. The reaction is typically carried out in a polar aprotic solvent like acetone or DMSO.

Step 5: Perform the reaction. Mix the isopropyl thiol and isopropyl halide under the specified conditions to yield the desired thioether product.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Thioether Formation

Thioethers are organic compounds containing a sulfur atom bonded to two alkyl or aryl groups. They can be synthesized through the nucleophilic substitution reaction of an alkyl halide with a thiol. The thiol acts as a nucleophile, attacking the electrophilic carbon of the alkyl halide, resulting in the formation of a thioether and the release of a halide ion.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution reactions can occur via two main mechanisms: SN1 and SN2. In SN2 reactions, a nucleophile attacks the electrophilic carbon from the opposite side of the leaving group, leading to a concerted reaction. In contrast, SN1 reactions involve the formation of a carbocation intermediate, followed by nucleophilic attack. Understanding these mechanisms is crucial for predicting the outcome of reactions involving alkyl halides.

Reactivity of Alkyl Halides

Alkyl halides are organic compounds where a halogen atom is bonded to an alkyl group. Their reactivity in nucleophilic substitution reactions depends on the structure of the alkyl group and the type of halogen. Primary alkyl halides typically undergo SN2 reactions, while tertiary halides favor SN1 mechanisms due to steric hindrance. Recognizing the type of alkyl halide is essential for determining the appropriate synthetic pathway for thioether preparation.

Watch next

Master The mechanism of Sulfide Synthesis. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

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.

Textbook Question

Many hunting dogs enjoy standing nose-to-nose with a skunk while barking furiously, oblivious to the skunk spray directed toward them. One moderately effective way of lessening the amount of odor is to wash the dog in a bath containing dilute hydrogen peroxide, sodium bicarbonate, and some mild dish detergent. Use chemical reactions to describe how this mixture helps to remove the skunk spray from the dog. The two major components of skunk oil are 3-methylbutane-1-thiol and but-2-ene-1-thiol.

Textbook Question

Thiols are prone to dimerize through the formation of a disulfide bond in a reaction that stylists use to induce permanent curls in hair. What type of reagent would you use to effect this transformation?

Textbook Question

Starting with hydrogen sulfide, suggest a synthesis of the following thioether that makes use of two different haloalkanes.

Textbook Question

Show how you would synthesize butyl isopropyl sulfide using butan-1-ol, propan-2-ol, and any solvents and reagents you need.

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.

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

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

Key Concepts

Thioether Formation

Nucleophilic Substitution Mechanisms

Reactivity of Alkyl Halides

Watch next

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