Nomenclature and Reactivity write the IUPAC surname of a thiol, offered its Kekulé, condensed or shorthand structure. Attract the structure of a thiol, offered its IUPAC name. Compose an equation to stand for the formation of a thiol through the reaction of hydrosulfide anion with an alkyl halide. Compose an equation to highlight the preparation of a thiol by the reaction the thiourea through an alkyl halide. create an equation to display the interconversion in between thiols and disulfides. write the surname of a sulfide, provided its structure. Attract the structure of a sulfide, provided its name. Write an equation showing how a sulfide may be prepared by the reaction the a thiolate anion on an alkyl halide. Recognize the product indigenous the reaction of a provided alkyl halide v a provided thiolate anion. Identify the reagents important to prepare a given sulfide. Create an equation to highlight the formation of a trialkylsulfonium salt indigenous a sulfide and also an alkyl halide.

Key Terms

de defiders mercapto group (organic) sulfide sulfone sulfoxide thiol thiolate anion trialkylsulfonium ion (trialkylsulfonium salt)

Study Notes

The centregalilee.comistry of sulfur-containing necessary compounds is regularly omitted from introduce organic centregalilee.comistry courses. However, us have included a quick section on these compounds, not for the sake of raising the amount of product to be digested, but due to the fact that much of the centregalilee.comistry of this substances have the right to be predicted native a understanding of your oxygen-containing analogues. A thiol is a compound which has an SH sensible group. The -SH group itself is called a mercapto group. A de defiders is a compound containing an -S-S- linkage. (Organic) sulfides have actually the structure R-S-R′, and also are therefore the sulfur analogues that ethers. The nomenclature that sulfides deserve to be easily understood if one understands the nomenclature that the corresponding ethers. Notification that the term “thio” is additionally used in inorganic centregalilee.comistry. Because that example, SO42− is the sulfate ion; if S2O32−, in which one of the oxygen atoms of a sulfate ion has been replaced by a sulfur atom, is referred to as thiosulfate. Thiolate anions, RS- , are analogous to alkoxy anions, RO- . Thiolate anions are far better nucleophiles than are alkoxy anions (see ar 11.5, pages 389-394 of the textbook). If you have trouble understanding why trialkylsulfonium ions are formed, think that them as being somewhat similar to the hydronium ions that are created by protonating water:


Later we shall see examples of tetraalkylammonium ions, R4N+, i m sorry again may be concerned as being comparable to hydronium ions. Sulfoxides and sulfones are derived by oxidizing necessary sulfides. You require not memorize the methods used to carry out these oxidations.

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Table 18.1, below, provides a rapid comparison that oxygen-containing and also sulfur-containing essential compounds.


Oxidation states of Sulfur Compounds

Oxygen assumes just two oxidation says in its necessary compounds (–1 in peroxides and also –2 in various other compounds). Sulfur, top top the various other hand, is uncovered in oxidation states varying from –2 come +6, as shown in the complying with table (some simple inorganic compounds are shown in orange).


Thiols are usually ready by utilizing the hydrosulfide anion (-SH) as a neucleophile in one SN2 reaction with alkyl halides.

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On trouble with this reaction is the the thiol product have the right to undergo a second SN2 reaction with second alkyl halide to produce a sulfide next product. This trouble can be addressed by making use of thiourea, (NH2)2C=S, as the nucleophile. The reaction first produces an alkyl isothiourea salt and also an intermediate. This salt is then hydrolyzed by a reaction with aqueous base.