6 Questions
Which suffix is added to the parent chain name when naming a thiol compound?
-thiol
What is the general formula for a thiol compound?
R−SH
What is the IUPAC name for CH3CH2SH?
Ethanethiol
Which thiol compound is also known as 'methyl mercaptan'?
Methanethiol
How is thiophenol named relative to a corresponding oxygen compound like phenol?
Thiophenol
What purpose does CH3CH2SH serve in natural gas?
As an odorant
Study Notes
Thiol Compounds: Naming Common Thiols
Introduction
Thiols, also known as mercaptans, are a class of organic compounds similar to alcohols and phenols but containing a sulfur atom in place of an oxygen atom. They are represented by the general formula R−SH, where R represents an alkyl or other organic substituent. Thiols are used in various applications, including as odorants in natural gas and as reagents in organic synthesis. In this article, we will focus on the naming of common thiol compounds according to the International Union of Pure and Applied Chemistry (IUPAC) nomenclature rules.
Naming Thiols
Thiols are named using the same rules as alcohols, with the parent chain being named as an alkane and the suffix "-thiol" added. For example, CH3CH2SH is called "ethanethiol". When a thiol is named relative to a corresponding oxygen compound, the prefix "thiol-" is used, as in the case of thiophenol.
Examples of Named Thiols
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Methanethiol: Also known as methyl mercaptan, CH3SH is the simplest thiol and is used as an odorant in natural gas to make gas leaks easier to detect.
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Ethanethiol: Also known as ethyl mercaptan, CH3CH2SH is used as an odorant in natural gas and is used in the synthesis of other thiols.
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Thiophenol: This thiol is named relative to phenol, with the prefix "thiol-" added. It is a commonly used thiol in organic synthesis.
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Mercaptoacetic acid: This thiol is named by adding the suffix "-thiol" to the parent chain, in this case, acetic acid. It is an important precursor in the synthesis of other thiols.
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Methanethiol: This thiol has a pKa of 10.33 and is a weak acid compared to alcohols.
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Ethanethiol: This thiol has a pKa of 10.61 and is also a weak acid compared to alcohols.
Conclusion
In summary, the naming of thiol compounds follows the same rules as alcohols, with the parent chain being named as an alkane and the suffix "-thiol" added. When a thiol is named relative to a corresponding oxygen compound, the prefix "thiol-" is used. Some common thiol compounds include methanethiol, ethanethiol, thiophenol, and mercaptoacetic acid.
Test your knowledge on naming common thiol compounds following the IUPAC nomenclature rules. Learn how to name thiols using alkane parent chains and the suffix '-thiol', as well as when to use the prefix 'thiol-' when naming relative to oxygen compounds.
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