Nomenclature of Organic Compounds – IUPAC with examples
Nomenclature is the process of naming living and non-living substances. The word comes from the Latin word ‘nomen’ which means name, and ‘calare’, i.e. call.
Internationally agreed principles are used for naming different compounds. However, it may vary from using common and colloquial terminologies to strict rules.
Nomenclature is used in every branch of science, and in this section, IUPAC nomenclature for organic compounds will be discussed.
What is IUPAC?
IUPAC stands for International Union of Pure and Applied Chemistry. It was founded in 1919 as a replacement for the International Congress of Applied Chemistry. The headquarters of this organisation is located in the USA.
IUPAC is the international governing body for standardising atomic weights, symbols, nomenclature, etc. of various chemicals. It develops and maintains such data to aid chemists and researchers across the globe. This organisation is also responsible for creating the IUPAC nomenclature for inorganic and organic compounds.
IUPAC Nomenclature of Organic Chemistry
IUPAC has a prolonged history of providing nomenclature to organic and inorganic compounds. This naming system has been developed to create a set of standardised names that are accepted across the globe. This avoids the confusion of scientists naming substances in different ways.
Under this IUPAC nomenclature of organic chemistry, there is a set of rules that every chemist must follow to name compounds belonging to particular groups.
Furthermore, IUPAC’s nomenclature of organic compounds has three sections - substituents, the length of the carbon chain, and chemical end. Here, the substituents represent functional groups attached to the primary carbon chain. This main carbon chain is the longest possible continuous one. Additionally, the chemical ending represents the molecule’s type.
IUPAC nomenclature decides the fundamental root name by using the longest continuous chain of carbon. After that, this root name is modified with assistance from various functional groups that substitutes carbon and hydrogen atoms in the main structure.
There are various ways to modify the root name of a compound according to its functional group. These are –
Substitutive: This is probably the most common way of modifying a compound’s root name. Moreover, functional groups of the highest priority modify the suffix. On the other hand, other groups or substituents adds prefixes to root names.
Functional Groups: Here, substances are named according to their highest priority conditional groups. For instance, ketone, alkyl halide, alcohol, etc.
Replacement: This process indicates when a carbon atom is getting replaced by another atom.
Conjunctive: It is used for combining named subunits.
Trivial: Due to their widespread use, some compounds are registered under IUPAC nomenclature according to their trivial names.
Creation of Systematic Names
Creating these systematic names is a complicated process. It requires following a step-by-step method to form a nomenclature of organic compounds.
These steps are –
1. Determine the Functional Group that Will be Cited as the Suffix
2. Locate the Longest Carbon Chain With the Required Functional Group and Add Up the Number of Carbon Atoms. It Will Determine the Prefix of A Compound’s Name.
Find out the senior-most among these structural components joined to the primary characteristic group.
Specify unsaturation, if there is any after naming the parent hydride.
Combine the suffix and parent hydride name to determine the principal characteristic group.
Categorise the substituents, and then organise them in alphabetical order according to their corresponding prefixes.
Add multiplicative prefixes without altering the current order. Then insert locants.
Figure out the chirality centre and other stereogenic units, namely double bonds.
Lastly, add stereo descriptors.
Additionally, complex substituents of any organic compound having a branched structure should be regarded as substituted alkyl groups. However, the carbon attached to this group is numbered 1.
According to IUPAC nomenclature methods, such complex substituents should be in the brackets of their corresponding compounds.
Format used for this purpose is – “locant + prefix + root + locant + suffix”.
Characteristic Groups
Root: This term specifies the total number of carbon atoms that exist in a long carbon chain of an organic compound. For instance, ‘meth’ refers to the chain with one carbon atom, and ‘non’ indicates nine carbon atoms in an organic compound.
Suffix: Suffix in IUPAC nomenclature refers to the functional group it belongs to and follows the root name. It is further segregated into two types - primary and secondary.
The primary suffix is used immediately following the root word. For example, alkanes, where ‘ane’ is the suffix used just after the root word.
A secondary suffix is written after the primary one. For instance, compounds with alcohol and alkane group attached to them will be termed as an alkanol, here ‘ol’ is the secondary suffix for the alcohol group.
To comply with IUPAC norms, a suffix is used as part of the name of a particular compound.
Prefix: Prefix is added in front of the root names of compounds under this nomenclature. The use of prefix is very useful, as it shows the existence of side chains and substituent groups of an organic molecule. Such prefixes provide an insight into the acyclic and cyclic nature of compounds.
Similar to the suffix, a prefix is also divided into two categories - primary and secondary. The primary prefix indicates the acyclic or cyclic nature of any organic compound. For example, ‘cyclo’ prefix is used for cyclic compounds.
A secondary prefix portrays the existence of substituent groups and side chains. A prominent example of its use is the CH3 group, which is known as a methyl group.
Nomenclature of Few Compounds
In this IUPAC name list below, the nomenclature of some common compounds has been discussed.
Alkanes: Alkane is a type of saturated hydrocarbon, and its formula is \[C_{n}H_{2n+ 2}\]. The suffix ‘ane’ is used to describe any alkane compound - for instance, methane, ethane, butane, etc. However, when one hydrogen is removed from the end of a chain, it changes the suffix ‘-ane’ to ‘-yl’.
Alkyl Halides: It is considered as a substituent of alkane chains. Alkyl halides are regarded as an equal of alkyl substituent in the parent numbering chains.
These Halogens are characterised by –
F = fluoro-
Cl = chloro-
Br = bromo-
I = iodo-
Alkene: Double bonds of unsaturated hydrocarbons are regarded as an alkene. Here, ‘ene’ indicates the shift to double bonds.
Thus, if there are any second bonds, then the suffix expands to include a prefix. This prefix indicates the number of bonds.
Formula of alkene is \[C_{n}H_{2n}\]. Examples of this compound are ethene, propane, etc.
Alkynes: Similar to the system mentioned above, when a double bond expands to a triple bond, the suffix ‘-yne’ is used. An example of this group is ethyne. The general formula of an alkyne is \[C_{n}H_{2n-2}\].
Alcohols: Alcohols are named after replacing the ‘–ane’ suffix with ‘-anol’. If there are more than once hydroxyl group, then, this suffix is expanded to include a proper prefix.
A common example of this group is anediol, anetriol, pentanol, butanediol, etc.
Ethers: Ethers are known with their common names. In order to find that, two alkyl groups are attached to an oxygen atom, and then put them in alphabetical order with space between names.
They are trailed by the word ether. Additionally, ‘di-’ prefix is used in case both alkyl groups are the same.
Some examples of this group are diethyl ether, ethyl methyl ether, etc.
FAQs on IUPAC Nomenclature of Organic Compounds
1. What is nomenclature?
Nomenclature is the process of naming substances, both living and non-living. Various principals agreed internationally are used for this purpose. These principals enforce a standardise rule and eradicate the problem of various names for a single compound. Nomenclature, in biological classification, a system of naming organisms. The species to which the organism belongs is indicated by two words, the genus and species names, which are Latinized words derived from various sources. According to popular belief, scientists consider scientific names universal in their use after they are assigned, however, ongoing research on the relationships of organisms and inquiries into the history of names, as well as disagreements among scientists about the validity of certain names, contradict this notion.
Many well-known species have multiple names due to the lack of standard methods of establishing new names, but international rules are promoting significant taxonomic stability by limiting name changes, using standard methods to establish new names, and providing a working standard for the designation of new species. It is the responsibility of respected committees to resolve disputes.
2. What is the full form of iupac?
IUPAC’s full form is the International Union of Pure and Applied Chemistry. It is the prevailing body responsible for regulating atomic weights, symbols, nomenclature, etc. of various chemicals. The body improves and keeps these data to aid chemists and researchers across the globe. The International Union of Pure and Applied Chemistry (IUPAC) is the world authority on chemical nomenclature, terminology (including the naming of new elements in the periodic table), standardized methods for measurement, atomic weights, and many other critically evaluated data. It develops and maintains Recommendations that create a common language for the global chemistry community. The scientific work of IUPAC is conducted largely through a formal Project System in which proposals from chemists around the world are peer-reviewed and, if meritorious, are approved and supported.
In addition, IUPAC has many other wide-ranging activities that ultimately impact both the chemical profession and the worldwide community as a whole. These include the publishing of technical reports, journals, books, databases, and other information resources that facilitate the conduct of scientific research, conferences, and the provision of awards for the recognition of scientific excellence. IUPAC is also involved in joint projects with other organizations; one of which is the Joint Committee for Guides in Metrology (JCGM).
3. Why is nomenclature vital for chemistry?
The number of organic and inorganic compounds is increasing every day. Therefore, if there are no rules and regulations in place, it will be very difficult to find any substance. Hence, with the help of this nomenclature, such problems can be circumvented. Chemistry nomenclature's primary purpose is to ensure that each chemical name refers to only one substance, nor should there be any ambiguity concerning which chemical compound it refers to.
As a secondary aim, we should ensure that all substances have a single name (although several alternative names may be acceptable in some cases). Depending on who the document is addressed to, the nomenclature used will differ. Accordingly, there is no perfect form, but instead, there are many forms that are most or least appropriate depending on the context. Often, a chemical compound can be identified by its common name when a particular set of circumstances. Nevertheless, there are a few occasions (for example, when building large indices) when a specific name must be assigned to each compound.
To understand chemistry nomenclature, it is necessary to recognize chemical composition, such as stoichiometry and the type of atoms that make up the compound. Separating the inorganic from the organic is the first step in importance. However, it is not always obvious how these two components differ. Even chemists have trouble understanding them.
According to historical definitions (two centuries ago), inorganic compounds are created by geological systems and organic compounds are found in biological systems. Inorganic chemistry is concerned with molecules lacking carbon, according to the modern definition of organic compounds. Chemistry students who study carbon-based materials, such as diamonds and graphite, tend to get confused, but we will leave that argument to the reader. In the following sections, we describe the current rules for the nomenclature of organic and inorganic molecules.
4. What is trivial nomenclature system?
A trivial nomenclature system involves a non-systematic approach while naming any compound. Typically, the terms used every day to describe an organic nor inorganic substance, are registered as its official name. Therefore, compounds that have derived their name via this system have a much simple name compared to others. Trivial nomenclature is a system of naming compounds based on their common names, which might be derived from the origin, a place, or even at random. HCOOH is known as formic acid because it is a molecule found in ants. HCOOH is called formic acid since it occurs naturally in ants. Since these molecules are commonly found in ants, HCOOH is often referred to as formic acid. Since these molecules are commonly found in ants, HCOOH is often referred to as formic acid. Because these molecules are commonly found in ants, HCOOH is also known as formic acid. In Latin, ants are called Formica. As a result of this system, it was possible for different people to give the same compound different names.
5. What are the rules for naming chemical compounds?
Following are the rules for naming chemical compounds:
The second element should be omitted, and the word "ide" should be added just like it is in ionic compounds.
The number of a given element within a compound is indicated by a prefix when naming molecular compounds. One will be represented by "mono-" and two by "di-"; three will be represented by "tri-"; four by "tetra-"; five by "penta-"; six by "hexa-"; seven by "hepta-"; nine by "nona-" and ten by "deca."
The prefix can be dropped if only one of the first elements exists. Carbon monoxide is not mono carbon monoxide, for instance.
In the case of a conflict between two vowels in a row once the prefix is added (they sound the same", the extra vowel is dropped). Monoxide, instead of monoxide, is the result of one oxygen. The additional o is dropped.
Most commonly, the atom with the higher electropositivity is written first, followed by the atom with the lower electropositivity with its suffix. Dihydrogen monoxide (though it's not typical to call it that) can also be called \[H_{2}O\] (water). These rules do not apply to organic molecules (molecules made up of C and H in combination with other elements).