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Ketone Naming

Ketone

Ketone

Ketone, any of a class of organic compounds characterized by the presence of a carbonyl group in which the carbon atom is covalently bonded to an oxygen atom. The remaining two bonds are to other carbon atoms or hydrocarbon radicals (R): Ketone compounds have important physiological properties. They are found in several sugars and in compounds for medicinal use, including natural and synthetic steroid hormones. Molecules of the anti-inflammatory agent cortisone contain three ketone groups. Only a small number of ketones are manufactured on a large scale in industry. They can be synthesized by a wide variety of methods, and because of their ease of preparation, relative stability, and high reactivity, they are nearly ideal chemical intermediates. Many complex organic compounds are synthesized using ketones as building blocks. They are most widely used as solvents, especially in industries manufacturing explosives, lacquers, paints, and textiles. Ketones are also used in tanning, as preservatives, and in hydraulic fluids. The most important ketone is acetone (CH3COCH3), a liquid with a sweetish odour. Acetone is one of the few organic compounds that is infinitely soluble in water (i.e., soluble in all proportions); it also dissolves many organic compounds. For this reason—and because of its low boiling point (56 °C [132.8 °F]), which makes it easy to remove by evaporation when no longer wanted—it is one of the most important industrial solvents, being used in such products as paints, varnishes, resins, coatings, and nail-polish removers. The International Union of Pure and Applied Chemistry (IUPAC) name of a ketone is derived by selecting as the parent the longest chain of carbon atoms that contains the carbonyl group. The parent chain is numbered from the end that Continue reading >>

1. Nomenclature Of Aldehydes And Ketones

1. Nomenclature Of Aldehydes And Ketones

Aldehydes and ketones are organic compounds which incorporate a carbonyl functional group, C=O. The carbon atom of this group has two remaining bonds that may be occupied by hydrogen or alkyl or aryl substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde. If neither is hydrogen, the compound is a ketone. The IUPAC system of nomenclature assigns a characteristic suffix to these classes, al to aldehydes and one to ketones. For example, H2C=O is methanal, more commonly called formaldehyde. Since an aldehyde carbonyl group must always lie at the end of a carbon chain, it is by default position #1, and therefore defines the numbering direction. A ketone carbonyl function may be located anywhere within a chain or ring, and its position is given by a locator number. Chain numbering normally starts from the end nearest the carbonyl group. In cyclic ketones the carbonyl group is assigned position #1, and this number is not cited in the name, unless more than one carbonyl group is present. If you are uncertain about the IUPAC rules for nomenclature you should review them now. Examples of IUPAC names are provided (in blue) in the following diagram. Common names are in red, and derived names in black. In common names carbon atoms near the carbonyl group are often designated by Greek letters. The atom adjacent to the function is alpha, the next removed is beta and so on. Since ketones have two sets of neighboring atoms, one set is labeled α, β etc., and the other α', β' etc. Very simple ketones, such as propanone and phenylethanone (first two examples in the right column), do not require a locator number, since there is only one possible site for a ketone carbonyl function. Likewise, locator numbers are omitted for the simple dialdehyde at t Continue reading >>

Ketones

Ketones

Nomenclature Formula 3D structure Functional class name = alkyl alkyl ketone Substituent suffix = -one e.g. propan-2-one Substituent prefix = oxo- The root name is based on the longest chain including the carbonyl group. The chain is numbered so as to give the ketone carbonyl the lowest possible number. The ketone suffix is appended after the hydrocarbon suffix minus the "e" : e.g. -ane + -one = -anone or -ene + one = -enone etc. Functional group is a ketone, therefore suffix = -one Hydrocarbon structure is an alkane therefore -ane The longest continuous chain is C5 therefore root = pent The first point of difference rule requires numbering from the left as drawn to make the ketone group locant 2- pentan-2-one or 2-pentanone CH3CH2CH2C(=O)CH3 window1._cover(false)Jmol._Canvas2D (Jmol) "window1"[x]loading... -- required by ClazzNode Continue reading >>

Naming Aldehydes

Naming Aldehydes

In the IUPAC system we use the -al ending. The end e is replaced by al. So the common names of the first four aldehydes become: Now this is all pretty simple, but what if there are side chains off the main aldehyde chain. For example, take the molecule pictured on the right. Step 1 The aldehyde forms the root name Step 2 Number the carbons so that the C=O is carbon number 1. Step 3 Name all the substituents in alphabetical order. 3-methylbutanal Consider the example shown on the right. It has two substituent groups, the methyl and hydroxy. The IUPAC name is 4-hydroxy-3-methylbutanal. When naming a ketone we remove the end "e" from the name and replace it with a "one". For example propane becomes propanone. Since the carbonyl group can be located anywhere in the carbon chain a locator number is needed. . With simple molecules, such as propanone, shown on the right, a number is not needed as there can be only one location for the carbonyl group. Now lets look at he steps to derive a IUPAC name. Step 1) Identify the longest carbon chain that contains the carbonyl group and number the carbons so that the carbonyl group is on the lowest carbon. Step 2) Identify the various substituent groups Step 3) Place the substituent groups in the name in alphabetical order and use position numbers to locate the substituent groups and the carbonyl group. Step 4) Change the end e to a one. Lets take the molecule shown on the right as an example. Step 1 The longest carbon chain is pentane Step 2 No substituent groups Step 3 and 4 The carbonyl group is found at carbon number 2 . Hence the name is 2-pentanone What is the IUPAC name of this molecule? Solution What is the IUPAC name of this molecule? Solution What is the IUPAC name of this molecule? Solution Continue reading >>

Weird Nomenclature In Carbonyl Chemistry

Weird Nomenclature In Carbonyl Chemistry

Making it through the chemistry of carbonyl derivatives (ketones, aldehydes, carboxylic acids, esters, and more) there are at least two “weird” nomenclature issues that repeatedly come up to baffle students: Greek letters, and “1,2-” or “1,4-” addition reactions. In this post I’ll try to address them both. 1. Greek letters The functional group C=O is called a “carbonyl”. The carbon itself is called the “carbonyl carbon”, and the oxygen is called “the carbonyl oxygen”. But what do you call a carbon adjacent to the carbonyl carbon… or 3 carbons away? In organic chemistry, it’s common to use Greek letters to denote this. So the carbon adjacent to a carbonyl is called an “α (alpha) carbon”, two carbons away is called a “β carbon”, and so on. This nomenclature can be used to depict different kinds of substituted carbonyl groups. For example a ketone with an OH on the beta carbon would be called a “β-hydroxy ketone”. If it was one carbon further down it would be a “γ hydroxy ketone”. If we have a double bond between the α carbon and the β carbon it’s common to call it “α,β-unsaturated”. So we can have α,β unsaturated ketones, aldehydes, esters, and so on. It can keep going beyond gamma, of course, but it’s rare to see it progress beyond ε (epsilon). Another thing: aldehydes, esters, carboxylic acids, and so on, can only have one “alpha” carbon each, wheras ketones can have two. Sometimes you’ll see one set of Greek symbols marked with ‘ (prime) symbols to distinguish them. The location of the prime is completely arbitrary. For esters, the OR group is not denoted “alpha”. It’s usually just called the “alkoxy” group. 1,2 and 1,4 additions Another item of confusion are the terms “1,2-addition” Continue reading >>

Nomenclature Of Aldehydes And Ketones

Nomenclature Of Aldehydes And Ketones

It is a basic rule in ketone nomenclature..... that when it is a straight chain compound or a cyclic compound , we drop off the 'e' from alkane and put 'one'... so a hexane becomes a hexanone .... however in presence of two ketone groups in a compound... (diones) the 'e' in alkane is retained and we add 'dione or trione ' to the IUPAC name.. (it says simply that in a single ketone group the two vowels clash, so a vowel is dropped off i.e 'e' ... else it would be hexaneone.. (which doesnt sound… (more) A phenyl group refers to an aromatic ring that is directly attached to the chain/group in question (think aniline, which can also be named phenylamine, Ar-NH2), whereas a benzyl group refers to an aromatic ring bonded to another carbon, the latter of which is then attached to the chain/group in question. So a phenyl alcohol (or phenol) is Ar-OH, and a benzyl alcohol is Ar-CH2-OH (where Ar stands for an aromatic ring, and the bolded part is the phenyl/benzyl group proper). So when you have two… (more) Hydrogens are assumed at any position where nothing is shown. We know that a carbon (without a formal charge) should be participating in four bonds. Since the carbons at each end of the double bond have three bonds shown and no charge, they must have a fourth bond to hydrogen that isn't being shown. Furthermore, the bonds to other carbons are shown and so there is only one 'space' left for each of the hydrogens we know must be present. Those spaces are on opposite sides of the double bond… (more) Because that's what we do to indicate the presence of double bonds between carbon atoms. Ethane has a single bond between carbon atoms Ethene has a double bond between carbon atoms Ethyne has a triple bond between carbon atoms (Note: alkAne, ethAne. alkEne, ethEne. alkYne, ethYn Continue reading >>

Chapter 14 - Aldehydes And Ketones

Chapter 14 - Aldehydes And Ketones

Sort Guide to naming ketones Step 1 name the longest carbon chain by replacing e with -one. Step 2 # carbon chain from end nearer to carbonyl group Step 3 name and number substituents Step 4 for cyclic ketones add prefix cyclo Continue reading >>

The Structure And Naming Of Aldehydes & Ketones

The Structure And Naming Of Aldehydes & Ketones

Doc Brown's GCE A Level AS A2 Chemistry Revising Advanced Level Organic Chemistry Revision Notes Part 5 CARBONYL COMPOUNDS NOMENCLATURE of ALDEHYDES and KETONES 5.1 The molecular structure and naming of ALDEHYDES and KETONES - including nomenclature of some isomers Nomenclature of aldehydes & ketones names and structures of aldehydes & ketones How to name aldehydes? How to name ketones? Nomenclature of substituted aldehydes or ketones - examples of acceptable names, displayed formula of aldehydes and ketones, graphic formula of aldehydes and ketones, molecular formula of aldehydes and ketones, skeletal formula of aldehydes and ketones, structural formula of aldehydes and ketones and homologous series of aldehydes and ketones, how to name the carbonyl group of compounds known as aldehydes and ketones Organic Chemistry Part 5 sub-index: 5.1.1 Nomenclature introduction * 5.1.2 Examples of aldehydes 5.1.3 Examples of ketones * 5.1.4 Other examples of substituted ketones 5.1.5 Oxidation sequence: alcohol ==> aldehyde/ketone ==> carboxylic acid Revision notes on the structure and naming-nomenclature of Aldehydes and Ketones 5.1.1 Introduction to Aldehyde and Ketone Nomenclature How do you name aldehydes? How do you name ketones? How do you name substituted aldehydes or ketones? Aldehydes and ketones are a group of compounds containing the carbonyl group, C=O. Aldehydes always have a hydrogen atom attached to the carbon of the carbonyl group, so the functional group is -CHO (see diagram above). The functional group is shown by using 'al' in the suffix part of the name e.g. methanal, ethanal, propanal etc. The prefix for the aldehyde name is based on the parent alkane minus the e. No number is required for the aldehyde group because the aldehyde group cannot be anything else ex Continue reading >>

Aldehydes And Ketones

Aldehydes And Ketones

Aldehydes are easily oxidized and more reactive than ketones. Ketones are more difficult to oxidize and are less reactive than aldehydes. The structure of the aldehyde and ketone is a sp2 NOMENCLATURE Aldehydes: common names The common names of aldehydes end with the word aldehyde and are based on the name of the carboxylic acid they are derived from. Aldehydes: IUPAC names The IUPAC names end with -al. The aromatic names of aldehydes are often derived from the common names. If there are two names listed, the first is the common and the second is IUPAC. If only one name is listed, it serves as both the IUPAC and common. Many times it is too difficult to name an aldehyde using the common names, so it defaults to the IUPAC system. But, many times the common name system of numbering is used in which Greek letters are substituted for the numbers. The carbonyl group always gets the number one position, while the Greek letters (a,b,g,d) are used in the common names starting at the second carbon (first available carbon for a side group). Ketones: Common names The simplest ketone is called acetone. The other names of ketones list the two groups on each side of the carbonyl group followed by the word ketone. A ketone in which the carbonyl group is attached to a benzene ring is named a -phenone. The longest chain containing the carbonyl group is considered the parent structure and the -e is replaced by -one. The carbonyl group is given the lowest possible number. PHYSICAL PROPERTIES The polar carbonyl group makes ketones and aldehydes polar. As the molecular weights increase, so do their melting and boiling points. They have lower boiling points than comparable alcohols or carboxylic acids. The lower aldehydes and ketones are appreciably soluble in water and borderline solubility Continue reading >>

Aldehydes And Ketones

Aldehydes And Ketones

The carbon atom of a carbonyl group must form two other bonds in addition to the carbon oxygen double bond in order to have four bonds. The nature of these two additional bonds determines the type of carbonyl containing compound it is. Aldehyde - In an aldehyde one of the two additional bonds that the carbonyl carbon atom forms must be ti a hydrogen atom. The other may be to a hydrogen atom, an alkyl or cycloalkyl group, or an aromatic ring system. Ketone - In a ketone both of the additional bonds of the carbonyl carbon atom must be to another carbon atom that is part of an alkyl, cycloalkyl or aromatic group. The carbonyl group of an aldehyde is flanked by a hydrogen atom, while the carbonyl group of a ketone is flanked by two carbon atoms. The systematic name for an aldehyde is obtained from the parent alkane by removing the final -e and adding -al. For ketones the final -e is replaced by -one, and a number indicates the position of the carbonyl group wherever necessary. The carbon chain in ketones is numbered such that the carbonyl carbon gets the lowest possible number. In aldehyde the carbonyl group is always at the end of the chain and is always assumed to be carbon number 1. The positions of the other substituents are specified by numbers as usual. The following examples illustrates these principles. The names in parentheses are common names that are used much more often than the systematic names. An alternative system for naming ketones specifies the substituents attached to the C=C group. For example, the compound 2-butanone is used in the system as described. However this molecule also can be named methyl ethyl ketone and is commonly referred to in industry as MEK (methyl ethyl ketone). 1. Oxidation Aldehyde are oxidized to carboxylic acids by a variety of oxi 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 >>

Naming Ketones

Naming Ketones

Naming Organic Compounds Series: Video 15 This Leah4sci tutorial video shows you how to name molecules containing a carbonyl in the middle of the chain using my puzzle piece approach to IUPAC nomenclature. Naming examples include simple and substituted ketones, multiple carbonyls and cyclic ketones. (Watch on YouTube: Ketones. Click CC on bottom right for transcript.) <– Watch Previous Video: Naming Aldehydes –> Watch Next Video: Naming Carboxylic Acids This is Video 15 in the Naming Organic Compounds Video Series. Click HERE for the entire series. Need a review on Functional Groups? Watch the Functional Groups Video then try the Functional Groups Quiz. Continue reading >>

Ketone

Ketone

Not to be confused with ketone bodies. Ketone group Acetone In chemistry, a ketone (alkanone) /ˈkiːtoʊn/ is an organic compound with the structure RC(=O)R', where R and R' can be a variety of carbon-containing substituents. Ketones and aldehydes are simple compounds that contain a carbonyl group (a carbon-oxygen double bond). They are considered "simple" because they do not have reactive groups like −OH or −Cl attached directly to the carbon atom in the carbonyl group, as in carboxylic acids containing −COOH.[1] Many ketones are known and many are of great importance in industry and in biology. Examples include many sugars (ketoses) and the industrial solvent acetone, which is the smallest ketone. Nomenclature and etymology[edit] The word ketone is derived from Aketon, an old German word for acetone.[2][3] According to the rules of IUPAC nomenclature, ketones are named by changing the suffix -ane of the parent alkane to -anone. The position of the carbonyl group is usually denoted by a number. For the most important ketones, however, traditional nonsystematic names are still generally used, for example acetone and benzophenone. These nonsystematic names are considered retained IUPAC names,[4] although some introductory chemistry textbooks use systematic names such as "2-propanone" or "propan-2-one" for the simplest ketone (CH3−CO−CH3) instead of "acetone". The common names of ketones are obtained by writing separately the names of the two alkyl groups attached to the carbonyl group, followed by "ketone" as a separate word. The names of the alkyl groups are written alphabetically. When the two alkyl groups are the same, the prefix di- is added before the name of alkyl group. The positions of other groups are indicated by Greek letters, the α-carbon being th Continue reading >>

Ketone Nomenclature

Ketone Nomenclature

The International Union of Pure and Applied Chemistry (IUPAC) has established rules to systematize the naming of ketone molecules. A brief summary of those rules is presented here. First identify the longest continuous chain of carbon atoms that includes the carbonyl (ketone) group. The ketone's IUPAC name corresponding to this chain of carbons is stated with the "e" on the end of the normal hydrocarbon name replaced by "one" (pronounced "own"). The chain is numbered such that it begins at the end of the molecule nearest the location of the carbonyl group. If each end of the molecule has a carbonyl group that would lead to an equivalent numbering scheme, determine the numbering scheme based on the end of the molecule that has the next-closest carbonyl as the end where numbering begins. A number is included to identify the location of each carbonyl in the chain. The numbers are separated by commas. A dash connects the number locations to the ketone name. Prefixes are added to the "one" ending when more than 1 ketone group is present. The first few prefixes for these are: When ketone molecules contain multiple bonds, they are numbered relative to the locations of the carbonyl group. butanone cyclopentanone 5,6-dimethyl-2,4-heptadione 4,4-diethyl-3-hexanone 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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