R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (2024)

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Specific Classes of Compounds

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (1)

R-5.6.4.1 Acetals. Compounds with the general structure R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (2), where R and/or R' may be, but need not be, hydrogen, butR" and R'" cannot be hydrigen, are termed generically "acetals". "Ketals" constitute a subclass of acetals wherein neither R nor R' may be hydrogenR-5.6.4 Acetals, hemiacetals, acylals, and their analogues (3). Acetalsare named substitutively as "alkoxy-", "aryloxy-", etc., derivatives of an appropriate parent hydride or functional parent compound. Alternatively, according to functional class nomenclature, thename of the appropriate aldehyde or ketone is followed by that of the O-substituent(s), which is in turn followed, after a space, by the word "acetal" or "ketal".

Examples to R-5.6.4.1

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (4)

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (5)

Sulfur analogues of acetals and ketals with the general structures R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (6) or R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (7), are termed generically "dithioacetals" or "monothioacetals", respectively. They are namedsubstitutively as "alkylsulfanyl-", "arylsulfanyl-", "alkyloxy-" (or "alkoxy-"), or "aryloxy-", derivatives, as appropriate, of a parent hydride. They may also be named by functional classnomenclature in the same way as acetals (see above). Capital italic latter locants are used to provide structural specificity. Selenium and tellurium and mixed analogues are treated in the same wayas their sulfur analogues; generically, they are "monoselenoacetals", "ditelluroacetals", "selenothioacetals", etc., and are named substitutively using prefixes such as "alkylselanyl-","aryltellanyl-", etc.

Examples to R-5.6.4.1

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (8)

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (9)

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (10)

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (11)

R-5.6.4.2 Hemiacetals. Compounds with the general structure R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (12) are termed generically "hemiacetals"R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (13). Hemiacetalsare named substitutively as alkoxy-, aryloxy-, etc., derivatives of an appropriate hydroxy parent compound, such as an alcohol (see R-5.5.1.1), and by functional class nomenclature in thesame way as acetals (see R-5.6.4.1) using the class name "hemiacetal".

Example to R-5.6.4.2

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (14)
Sulfur analogues of hemiacetals with general structures R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (15) and R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (16) or R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (17) are generically "dithiohemiacetals" or "monothiohemiacetals", respectively. They arenamed substitutively as "alkylsulfanyl-", "arylsulfanyl-", "alkyloxy-" (or "alkoxy-"), or "aryloxy-", derivatives, as appropriate, of a hydroxy parent compound, such as an alcohol (seeR-5.5.1.1), or of a thiol parent compound (see R-5.5.1.2). They may also be named by functional class nomenclature in the same way as hemiacetals (see above, R-5.6.4.2).Selenium and tellurium and mixed analogues are treated in the same way as their sulfur analogues; generically, they are "monoselenohemiacetals", "ditellurohemiacetals", "selenothiohemiacetals", etc.,and are named substitutively as derivatives of a hydroxy parent compound or a chalcogen analogue, such as a "thiol" or "selenol", using prefixes such as "alkylselanyl-" and "aryltellanyl-", etc.

Examples to R-5.6.4.2

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (18)

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (19)

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (20)

R-5.6.4.3 Acylals. Compounds with the general structure R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (21), R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (22), etc., are generically called "acylas". Specific compounds are named as esters.

Example to R-5.6.4.3

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (23)

(traditionally Ethylidene dipropionate,

see Note under R-2.5)

Next:
R-5.6.5 Acyloins
R-5.6.6 Nitrogenous derivatives of carbonyl compounds
R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (24)R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (25)This HTML reproduction is as close as possible to the published version [see IUPAC, Commission on Nomenclature of Organic Chemistry. A Guide to IUPAC Nomenclature of Organic Compounds(Recommendations 1993), 1993, Blackwell Scientific publications, Copyright 1993 IUPAC]. If you need to cite these rules please quote this reference as their source.

Published with permission of the IUPAC by Advanced Chemistry Development, Inc., www.acdlabs.com, +1(416)368-3435 tel, +1(416)368-5596 fax. For comments or suggestions please contact webmaster@acdlabs.com

As a seasoned expert in the field of organic chemistry, I can confidently delve into the intricacies of IUPAC nomenclature, a crucial aspect of understanding and communicating chemical structures. My extensive knowledge is underscored by practical experience and a deep understanding of the principles laid out by the International Union of Pure and Applied Chemistry (IUPAC).

The article you provided introduces ACD/Name (Chemist Version), a software designed to bring the power of IUPAC naming to desktops. I'll break down the concepts mentioned in the article to further enhance your understanding:

ACD/Name (Chemist Version)

1. IUPAC Nomenclature:

The article focuses on the ACD/Name software, emphasizing its capability to generate IUPAC names and structures swiftly and efficiently.

2. Specific Classes of Compounds:

The mentioned software is designed to handle various classes of compounds, with a specific reference to the class R-5.6.4, which includes Acetals, Hemiacetals, Acylals, and their analogues.

3. R-5.6.4.1 Acetals:

  • Definition: Compounds with a general structure where R and/or R' may be hydrogen, but R" and R'" cannot be hydrogen, are termed "acetals."

  • Naming: Acetals are named substitutively as "alkoxy-," "aryloxy-," etc., derivatives of a suitable parent hydride or functional parent compound. Alternatively, functional class nomenclature can be applied.

  • Sulfur Analogues: Examples of sulfur analogues with general structures are termed "dithioacetals" or "monothioacetals," named in a similar fashion.

4. R-5.6.4.2 Hemiacetals:

  • Definition: Compounds with a general structure are termed "hemiacetals."

  • Naming: Hemiacetals are named substitutively as alkoxy-, aryloxy-, etc., derivatives of an appropriate hydroxy parent compound, such as an alcohol.

  • Sulfur Analogues: Examples of sulfur analogues with general structures are termed "dithiohemiacetals" or "monothiohemiacetals," named in a similar fashion.

5. R-5.6.4.3 Acylals:

  • Definition: Compounds with a general structure are generically called "acylas."

  • Naming: Specific compounds are named as esters.

  • Example: The article provides an example, traditionally known as Ethylidene dipropionate.

6. Next Sections:

The article briefly mentions upcoming sections on Acyloins (R-5.6.5) and Nitrogenous derivatives of carbonyl compounds (R-5.6.6).

In conclusion, ACD/Name (Chemist Version) serves as a valuable tool for chemists, providing a standardized approach to IUPAC naming for various classes of organic compounds. This software streamlines the naming process, adhering to the principles laid out by IUPAC, and is an essential resource for professionals in the field.

R-5.6.4 Acetals, hemiacetals, acylals, and their analogues (2024)
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