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How Do You Name A Ketone As A Substituent?

Ketones

Ketones

Abstract As already mentioned in Chapter 20, which deals with aldehydes, compounds containing the carbonyl group (>C=O, commonly written CO) attached to two carbon atoms are called ketones. In that chapter the close structural relationship between aldehydes and ketones is pointed out, and the need in systematic nomenclature to distinguish between these two types of carbonyl compounds is questioned. Nevertheless, since modern usage continues to reflect the desire of organic chemists to treat aldehydes and ketones as two separate functional classes and since no official approval has yet been given to proposals for a unified nomenclature, the traditional approach is retained in this book. Also included in this chapter are thioketones, which contain the thiocarbonyl group (>C=S), and quinones, which are a sub-class made up of cyclic unsaturated ketones having two carbonyl groups directly attached to a six-membered ring containing two double bonds. Structures in which an ester, amide, or anhydride Continue reading >>

Ketone Nomenclature

Ketone Nomenclature

Video Transcript Hey guys! Let’s learn how to name ketones. Ketones are going to modify the root name of a carbon chain. You’re going to take out the e ending of the carbon courage chain and then you’re replace it with the suffix -one. I know that looks like one. Please do not say one. It’s pronounced -one like ketone. In this video, we're not going to discuss the prioritization of all functional groups in terms of numbering locations but just suffice it to say that ketones are going to have higher priority than pretty much all the groups you learned in Orgo 1, including alcohols. If you saw an alcohol and a ketone next to each other, and you had to figure out which one gets the higher priority with naming and numbering, you would pick the ketone. There’s IUPAC name and there’s common names. When you're assigning common names to ketones, then you’re going to name both of the R-groups alphabetically here and you’re going to end with the word ketone. Let me just show you a really quick example of the difference between common and IUPAC. Let’s say you have a four-carbon chain with a carbonyl in the middle. In IUPAC, the name of this would be, it starts off as a butane, now it's going to be a butanone and you have to name the location because I need to know exactly where that ketone is. It could be anywhere. I’m going to name this as a 2-butanone. That would be IUPAC. In terms of common naming, it would be a little different. For the common name, you would just name the substituents in alphabetical order and end with the word ketone. Then it would be on ethyl methyl ketone, almost like it’s an ether. Remember that ethers you can do that as well. You can name both of the substituents and end with ether. This would be an ethyl methyl ketone. This common Continue reading >>

Try To Name The Following Compound Using These Conventions�

Try To Name The Following Compound Using These Conventions�

a. Ketones are named by dropping the -e ending of the parent name and adding -one. The substituent name for the O= group is oxo. Ketones can also be named by naming each of the two carbon groups as a separate word followed by a space and the word ketone. b. Ring compounds can be named by dropping the -e ending of the parent name and adding -one. c. Common names that you should know are... d. The Greek letters a, b, g, etc. are used at times to designate attached groups on the second, third and fourth, etc. carbons from the carbonyl. This nomenclature is common for many functional groups such as aldehydes, carboxylic acids and derivatives of carboxylic acids. Copyright � August 2000 by Richard C. Banks...all rights reserved. Continue reading >>

Iupac System And Iupac Rules Of Naming Aldehydes & Ketones

Iupac System And Iupac Rules Of Naming Aldehydes & Ketones

The IUPAC names of open chain aliphatic aldehydes and ketones are derived from the names of the corresponding alkanes by replacing the ending -e with -al and -one respectively. a) The longest carbon chain containing the carbonyl carbon is taken to decide the name of the parent alkane. b) The carbon chain is numbered from the end nearer to the carbonyl group and the substituents are prefixed in alphabetical order along with Arabic numerals including their positions in the carbon chain. The carbon of the aldehydic group and the carbonyl carbon in cyclic ketones always get the number 1. c) When the aldehyde group is attached to a ring, the numbering of the ring carbon atoms starts from the carbon atom attached to the aldehyde group. The suffix carbaldehyde is added after the full name of the hydrocarbon. The simplest aromatic aldehyde carrying the aldehyde group on a benzene ring is benzaldehyde. Other ring substituted aromatic aldehydes are derivatives of benzaldehyde is ortho-hydroxy benzaldehyde. The trivial names of aldehydes are derived from the trivial names of the corresponding carboxylic acids by replacing the ending ic, for acid with aldehyde. The positions of the substituents in the carbon chain are indicated by Greek letters a, b, g, d etc, the a-carbon being the one directly linked to the aldehyde group, theb-carbon the next and on. The common names of ketones are derived by adding the names of the alkyl or aryl groups directly linked to the carbonyl group before the word ketone. The simplest ketone is acetone. The positions of the substituents are indicated by the Greek letters a, a', b', b' and so on. a, a' carbons being the ones directly attached to the carbonyl group. Ketones with a carbonyl group attached to a benzene ring are named as phenones in the IUPA Continue reading >>

Ketones Rule C-313

Ketones Rule C-313

Aldehydes, Ketones, and their Derivatives 313.1 - The name of a ketone having a ring or rings attached to a chain which contains the carbonyl group or groups is formed from the name of the corresponding acyclic hydrocarbon, with the radical name of the ring system as a substituent, the ketone group or groups being indicated by a suffix "-one", "-dione", etc. Examples to Rule C-313.1 313.2 - Acyclic monoacyl derivatives of cyclic compounds are named (a) by the method of Rule C-313.1, (b) by the radicofunctional method of Rule C-312.2, (c) by prefixing the name of the acyl group to the name of the cyclic component, or (d) if the cyclic component is benzene or naphthalene by changing the ending "-ie acid" or "-oie acid" of the name of the acid corresponding to the acyl group to "-ophenone" or "-onaphthone", respectively. Examples to Rule C-313.2 Exceptions: The following are examples of trivial names retained for ketones: 313.3 - When a carbonyl group is attached directly to carbon atoms in two ring systems, the compound is named by the radicofunctional method provided that no other substituent is present having priority for citation as principal group (compare Rule C-316.2). Examples to Rule C-313.3 Exception: 313.4 - The name of a polyketone in which two or more contiguous carbonyl groups have rings attached at each end is formed (a) by the radicofunctional method with the functional class name "diketone", "triketone", etc., or (b) by substitutive nomenclature with "-one" suffixes. Examples to Rule C-313.4 Exceptions: See Recommendations'93 R-5.6.2 This HTML reproduction of Sections A, B and C of IUPAC "Blue Book" is as close as possible to the published version [see Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H, Pergamon Press, Oxford, 1979. Copyri Continue reading >>

14.9 Aldehydes And Ketones: Structure And Names

14.9 Aldehydes And Ketones: Structure And Names

Learning Objectives Identify the general structure for an aldehyde and a ketone. Use common names to name aldehydes and ketones. Use the IUPAC system to name aldehydes and ketones. The next functional group we consider, the carbonyl group, has a carbon-to-oxygen double bond. Carbonyl groups define two related families of organic compounds: the aldehydes and the ketones. Note The carbonyl group is ubiquitous in biological compounds. It is found in carbohydrates, fats, proteins, nucleic acids, hormones, and vitamins—organic compounds critical to living systems. In a ketone, two carbon groups are attached to the carbonyl carbon atom. The following general formulas, in which R represents an alkyl group and Ar stands for an aryl group, represent ketones. In an aldehyde, at least one of the attached groups must be a hydrogen atom. The following compounds are aldehydes: In condensed formulas, we use CHO to identify an aldehyde rather than COH, which might be confused with an alcohol. This follows the general rule that in condensed structural formulas H comes after the atom it is attached to (usually C, N, or O). The carbon-to-oxygen double bond is not shown but understood to be present. Because they contain the same functional group, aldehydes and ketones share many common properties, but they still differ enough to warrant their classification into two families. Continue reading >>

Table Of Functional Group Priorities For Nomenclature

Table Of Functional Group Priorities For Nomenclature

Here’s a little nomenclature dilemma. Let’s say you’re trying to name a molecule. You’re familiar with the familiar naming suffixes like -ol, -ene, -ane, -oic acid and so on. But then you come across a molecule which has multiple functional groups. What do you do? What suffix do you give the molecule? We need some kind of priority system for nomenclature. And so, IUPAC has developed one. If you have a molecule with, say, a carboxylic acid and a ketone you consult the table. The functional group with the highest priority will be the one which gives its suffix to the name of the molecule. So in example #1 above, the suffix of the molecule will be “-oic acid” , not “-one”, because carboxylic acids are given higher priority. However, if a ketone is present with an alcohol (example 3) then we will use the suffix, “-one” because ketones have a higher priority for nomenclature than alcohols. [You might ask: what is this based on? It’s an arbitrary agreement by IUPAC [source], although note that there is some correlation between the oxidation state of the carbon and the priority (more oxidized groups tend to be higher priority). However this really is an example of something you have to either look up , memorize, or have a computer do for you. It’s not conceptual. ] Here it is: Table of Functional Group Priorities For Nomenclature Here are some examples of applying the order of functional group priorities to solve nomenclature problems. The highest ranked functional group becomes the suffix – it’s highlighted in red. This covers most of the functional groups you’ll meet in Org1/Org2, if you run into a thioketone or some other bizarre entity, you’ll probably want to see Reusch or Wikipedia. Organic Chemistry 2 builds on the concepts from Org 1 and Continue reading >>

Oxo Compounds

Oxo Compounds

Compounds containing an oxygen atom, =O, doubly bonded to carbon or another element. The term thus embraces aldehydes, carboxylic acids, ketones, sulfonic acids, amides and esters. Oxo used as an adjective (and thus separated by a space) modifying another class of compound, as in oxo carboxylic acids, indicates the presence of an oxo substituent at any position. To indicate a double-bonded oxygen that is part of a ketonic structure, the term keto is sometimes used as a prefix, but such use has been abandoned by IUPAC for naming specific compounds. A traditional use of keto is for indicating oxidation of CHOH to C=O in a parent compound that contains OH groups, such as carbohydrates, e.g. 3-ketoglucose. Cite as: IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. Original PDF version: The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable. Oxoacids (and its variants oxyacids, oxo acids, oxy-acids, oxiacids, oxacids) is a traditional name for any acid having oxygen in the acidic group. The term stands in contradistinction to `hydracids' (e.g. HCl) lacking oxygen. The term oxoacid now refers to a compound which contains oxygen, at least one other element, and at least one hydrogen bound to oxygen, and which produces a conjugate base by loss of positive hydrogen ion(s) (hydrons). E.g. P(OH)3 , RC(=O)OH , HOSOH , HOCl , HON=O , (HO)2SO2 , RP(=O)(OH)2 . Cite as: IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Continue reading >>

Naming Of Organic Compounds

Naming Of Organic Compounds

Nomenclature rules for different groups of organic compounds and functional groups, together with examples of use of the rules There are millions of different organic compounds and it is obvious that a systematic way of naming them is necessary. This article gives definitions of the different classes of organic compounds and rules for their naming together with many examples of use of the naming rules. See also naming of inorganic binary compounds. Content (links directly to the compound classes) Acyl halides Ethers Alcohols Functional groups priority Aldehydes General naming principles Alkanes Greek numbers used as prefixes Alkenes Haloalkanes (alkylhalides) Alkynes Ketones Amides Nitriles Amines Nitros Aromatics Sulfides (thioethers) Carboxylic acids Thiols (mercaptans) Esters Thiones (thioketones) General naming principles Organic compounds follow a certain naming pattern Prefix = substituent(s) Second Name = type of chain In the naming process we start with the First name: The core skeleton of an organic compound is called its root or parent chain. This refers to the simple skeleton or backbone of the molecule, upon which all the functional groups and substituents are attached. This is the first component to name and identify. The root chain is the longest continuing carbon chain in a molecule. Sometimes the root chain will be written in a simple manner and sometimes the chain will wind and twist. But as long as the carbons are connected, this is considered the parent chain. Then we find the Second name: The second name comes from the saturation of the parent chain, specifically the presence and location of double and triple bonds. These molecules fall into 3 categories: Alkane: Last name -ane Alkene: Last name -ene Alkyne: Last name -yne Then we identify prefixes: Continue reading >>

The Names Of Aromatic Compounds

The Names Of Aromatic Compounds

This page looks at the names of some simple aromatic compounds. An aromatic compound is one which contains a benzene ring. It assumes that you are reasonably confident about naming compounds containing chains of carbon atoms (aliphatic compounds). Note: If you aren't sure about naming aliphatic compounds follow this link before you go on. Naming aromatic compounds isn't quite so straightforward as naming chain compounds. Often, more than one name is acceptable and it's not uncommon to find the old names still in use as well. Background The benzene ring All aromatic compounds are based on benzene, C6H6, which has a ring of six carbon atoms and has the symbol: Each corner of the hexagon has a carbon atom with a hydrogen attached. Note: If you don't understand this structure, it is explained in full in two pages on the structure of benzene elsewhere in this site. Following this link could well take you some time! The phenyl group Remember that you get a methyl group, CH3, by removing a hydrogen from methane, CH4. You get a phenyl group, C6H5, by removing a hydrogen from a benzene ring, C6H6. Like a methyl or an ethyl group, a phenyl group is always attached to something else. Aromatic compounds with only one group attached to the benzene ring Cases where the name is based on benzene chlorobenzene This is a simple example of a halogen attached to the benzene ring. The name is self-obvious. The simplified formula for this is C6H5Cl. You could therefore (although you never do!) call it phenyl chloride. Whenever you draw a benzene ring with one other thing attached to it, you are in fact drawing a phenyl group. In order to attach something else, you have to remove one of the existing hydrogen atoms, and so automatically make a phenyl group. nitrobenzene The nitro group, NO2, i Continue reading >>

Parent Chain

Parent Chain

How to name organic compounds using the IUPAC rules In order to name organic compounds you must first memorize a few basic names. These names are listed within the discussion of naming alkanes. In general, the base part of the name reflects the number of carbons in what you have assigned to be the . The suffix of the name reflects the type(s) of functional group(s) present on (or within) the parent chain. Other groups which are attached to the parent chain are called substituents. Alkanes - saturated hydrocarbons The names of the straight chain saturated hydrocarbons for up to a 12 carbon chain are shown below. The names of the substituents formed by the removal of one hydrogen from the end of the chain is obtained by changing the suffix -ane to -yl. Number of Carbons Name 1 methane 2 ethane 3 propane 4 butane 5 pentane 6 hexane 7 heptane 8 octane 9 nonane 10 decane 11 undecane 12 dodecane There are a few common branched substituents which you should memorize. These are shown below. Identify the longest carbon chain. This chain is called the parent chain. Identify all of the substituents (groups appending from the parent chain). Number the carbons of the parent chain from the end that gives the substituents the lowest numbers. When compairing a series of numbers, the series that is the "lowest" is the one which contains the lowest number at the occasion of the first difference. If two or more side chains are in equivalent positions, assign the lowest number to the one which will come first in the name. If the same substituent occurs more than once, the location of each point on which the substituent occurs is given. In addition, the number of times the substituent group occurs is indicated by a prefix (di, tri, tetra, etc.). If there are two or more different substituen Continue reading >>

Organic Chemistry/naming

Organic Chemistry/naming

There are thousands of known organic compounds and millions of others yet to be discovered. Because of the wide variety of compounds a naming system was developed by International Union of Pure and Applied Chemistry (IUPAC)[1] to give a unique descriptive name to each compound. In this system the name of the compound directly shows its structure through an elaborate system of suffixes and prefixes. Common names are used for compounds that were either around before IUPAC or who have a more widely known name than the IUPAC. For example, trichloromethane is IUPAC name for chloroform, though it is almost universally referred to by students and scientists alike as chloroform. 1 Naming parent chains The IUPAC nomenclature of organic molecules is based on the longest carbon chain in the molecule. For alliphatics, which are hydrocarbons containing chains of C, the following prefixes are used: # of C Stem name Alkyl group name 1 meth methyl 2 eth ethyl 3 prop propyl 4 but butyl 5 pent pentyl 6 hex hexyl 7 hept heptyl 8 oct octyl 9 non nonyl 10 dec decyl 11 undec undecyl 12 dodec dodecyl Alkanes are a compound in which the carbon backbone contains only single bonds. They are named according to the number of carbons they have. Alkanes combust to produce water and carbon dioxide in air. Some familiar alkanes are methane (natural gas), propane (gas used in homes), and butane (blue-flamed cigarette lighters). Alkanes containing four carbons or more can form different chain isomers; that is, they can become "branched," forming, for example, iso-butane. General Alkane Formula: CnH2n+2 Suffix: "ane" Example: CH3CH2CH3 - Propane To name branched molecules, find the longest continuous chain first. This chain forms the base name. Number the carbon atoms, starting at the end closest to the Continue reading >>

Polyfunctional Compounds

Polyfunctional Compounds

Nomenclature of Compounds containing Polyfunctional Groups Organic compounds that contain two or more functional groups are called polyfunctional compounds. Some examples of organic compounds with polyfunctional groups are given below : Organic compounds containing polyfunctional groups example Let us now study how such compounds are named : Principal functional group In a polyfunctional compound, one of the functional groups is selected as the principal functional group while all other functional groups are treated as substituents. Functional groups according to their priorities are listed in the priority table in decreasing order i.e., Carboxylic acid with the highest priority is placed at the top while alkyne being the least in priority is placed at the bottom. The functional group which has the highest priority among all the functional groups present in an organic compound is selected as the principle functional group. [HIGHER to LOWER] PRIORITY TABLE COMPOUND NAME FORMULA Carboxylic acid -COOH Sulphonic acid -SO3H Ester -COOR Acid chloride -COCl Acid amides -CONH2 Nitrile -CN Aldehyde -CHO Ketone >C=O Alcohol -OH Phenol -C6H6O Thiols -SH Amines -NH2 Ether -OR Alkene >C=C< Alkyne -C≡C- All functional groups other than the principal functional group present in an organic compound are called substituents. In the following example, COOH being highest in priority is selected as the principal functional group while all others are treated as substituents. Some of the substituents with their prefixes are given below : Substituents SECONDARY FUNCTIONAL GROUP PREFIX -X (F,Cl,Br,I) Halo (fluoro, chloro, bromo, iodo ) -OH Hydroxy -SH Mercapto -OR Alkoxy -NH2 Amino -CHO Formyl or alkanoyl -C=O Keto or oxo -COOH Carboxy -COOR Alkoxycarbonyl or carbalkoxy -COCl Halocarbonyl or Continue reading >>

Organic Nomenclature

Organic Nomenclature

This document contains a highly compressed, simplified version of the naming rules put out by the International Union on Pure and Applied Chemistry (IUPAC). That's right, I said simplified. The actual rules must cover perfectly accurately all 20 million or so compounds discovered to date, and all 10 million or so that we will discover over the next decade or so. They are mind-bogglingly complex (to steal a phrase from Douglas Adams). The rules here are intended to work well on simple compounds, and to give the introductory student a flavor for how the system works. The naming of a compound follows several basic steps: Identify the functional groups present and assign them priority. Identify the highest priority substituent. Identify a parent portion of the molecule; name and number it. Identify the substituents and locate them on the numbered parent Assemble the name in proper order, and with proper punctuation, etc. Identify Functional Groups and Assign Priority The first step is to identify the functional groups present in the molecule. The following table has a large number of functional groups ranked in priority order. You should know that the highest priority group in your compound (towards the top of the table) is treated differently from the rest of the functional groups in the molecule. Note that some functional groups appear to have two or more carbon-containing groups; be sure you pay attention to which side of the functional group is the "main" side and which is the secondary side. For example, the "main" part of the ester group as shown below contains the R group; the secondary side contains the R' group. The main part of the functional group will be included in the parent. Carboxylic acid -oic acid* propanoic acid propionic acid Salt of acid -oate* sodium e Continue reading >>

Aldehydes And Ketones

Aldehydes And Ketones

Introduction We will focus more specifically on the organic compounds that incorporate carbonyl groups: aldehydes and ketones. Key Terms Aldehyde Formyl group Ketone Hydrogen bonding Hydration Hydrate Objectives Identify IUPAC names for simple aldehydes and ketones Describe the boiling point and solubility characteristics of aldehydes and ketones relative to those of alkanes and alcohols Characterize the process of nucleophilic addition to the carbonyl group The carbonyl group is shown below in the context of synthesizing alcohols. This functional group is the key component of aldehydes and ketones, which we will discuss here. Nomenclature for Aldehydes and Ketones Aldehydes and ketones are structurally similar; the only difference is that for an aldehyde, the carbonyl group has at most one substituent alkyl group, whereas the carbonyl group in a ketone has two. Several examples of aldehydes and ketones are depicted below. Aldehydes are named by replacing the -e ending of an alkane with -al (similarly to the use of -ol in alcohols). The base molecule is the longest carbon chain ending with the carbonyl group. Furthermore, the carbon atom in the carbonyl group is assumed to be carbon 1, so a number is not needed in the IUPAC name to identify the location of the doubly bonded oxygen atom. If the chain contains two carbonyl groups, one at each end, the correct suffix is -dial (used in the same manner as -diol for compounds with two hydroxyl groups). An example aldehyde is shown below with its IUPAC name. One- and two-carbon aldehydes have common names (one of which you will likely be familiar with) in addition to their systematic names. Both names are acceptable. Sometimes, the carbonyl group plus one proton (called a formyl group) must be treated separately for nomenclatu Continue reading >>

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