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Ch.20 - Electrochemistry
Chapter 20, Problem 106b

Disulfides are compounds that have S ¬ S bonds, like peroxides have O ¬ O bonds. Thiols are organic compounds that have the general formula R ¬ SH, where R is a generic hydrocarbon. The SH- ion is the sulfur counterpart of hydroxide, OH-. Two thiols can react to make a disulfide, R ¬ S ¬ S ¬ R. (b) What is the oxidation state of sulfur in a disulfide?

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insert step 1> Identify the general formula for a disulfide, which is R-S-S-R, where R represents a hydrocarbon group.
insert step 2> Recognize that in a disulfide, the sulfur atoms are bonded to each other and to carbon atoms from the hydrocarbon groups.
insert step 3> Recall that the oxidation state of sulfur in thiols (R-SH) is typically -2, as sulfur is more electronegative than hydrogen.
insert step 4> Consider that when two thiols form a disulfide, the S-S bond is formed, and the oxidation state of sulfur changes.
insert step 5> Determine the oxidation state of sulfur in the disulfide by considering that the S-S bond is a covalent bond between two sulfur atoms, and each sulfur atom shares one electron with the other, leading to an oxidation state of -1 for each sulfur in the disulfide.

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Key Concepts

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

Oxidation State

The oxidation state, or oxidation number, is a measure of the degree of oxidation of an atom in a compound. It indicates the number of electrons an atom has gained, lost, or shared when forming a chemical bond. In disulfides, understanding the oxidation state of sulfur is crucial for determining its chemical behavior and reactivity.
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Oxidation Numbers

Disulfide Bond

A disulfide bond is a covalent bond formed between two sulfur atoms, typically represented as S-S. This bond is significant in biochemistry, particularly in stabilizing the structure of proteins. In the context of the question, recognizing the nature of the disulfide bond helps in analyzing the oxidation states of the sulfur atoms involved.
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Thiols and Their Reactions

Thiols are organic compounds containing a sulfhydryl group (-SH) and are characterized by their strong odor and reactivity. When two thiols react, they can form a disulfide bond through oxidation, resulting in the release of hydrogen. Understanding this reaction is essential for determining the oxidation state of sulfur in disulfides, as it illustrates the transformation of thiols into disulfides.
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