diabetestalk.net

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 >>

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 >>

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 >>

Naming Ketones

Naming Ketones

Ketones are organic chemical compounds that include a -carbonyl group (i.e. an oxygen atom attached to a carbon atom by a double covalent bond) such that the carbon atom to which the -carbonyl group is attached is itself attached to two other carbon atoms - as opposed to one other carbon atom and one hydrogen atom, which the case for aldehydes That is, ketones are a class or category of organic chemical compounds that include a carbon atom attached to both an oxygen atom (by a double covalent bond), and also to two other carbon atoms (by a single covalent bond in each case). Bearing in mind that carbon atoms form a total of 4 single covalent bonds - or equivalent in combinations of double or triple bonds, a carbon atom attached to both an oxygen atom (by a double covalent bond) and also to two other carbon atoms (by a single covalent bond in each case) cannot be the first- or last - (which are equivalent positions) carbon atom in the chain of carbon atoms that form the organic molecule of which it is a part. This position of the -carbonyl group (oxygen atom) attached to a carbon atom that is not the last carbon atom in a carbon-chain is important because it distinguishes ketones from a similar category of organic compounds, called aldehydes. In contrast to ketones, aldehydes include a -carbonyl group attached to the end-carbon in a carbon-chain. Ketone molecules can vary in size up to very long molecules most of which consist of carbon atoms attached to each other and also to hydrogen atoms. 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 >>

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 >>

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 >>

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 >>

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 >>

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 >>

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 >>

Nomenclature

Nomenclature

IUPAC Names The naming of ketones is actually fairly simple, if you use the IUPAC method. It is very similar to the naming of alcohols. You start by choosing the longest carbon chain you can find that includes the carbon from the carbonyl group and use the length of that carbon chain as your base name. You change the ending by removing the -e and adding -one, and adding a number at the beginning of the name to indicate which carbon is double bonded to the oxygen. Then, if there are any side groups attached to the main chain, those are added to the front of the name with the appropriate numbers to show their location. Example A specific example is shown here (from Example 12-b in your workbook): butanone is formed from 2-butanol. The carbon chain is four carbon atoms long. Therefore, we have "butane" as a starting point. One of those carbons is double bonded to an oxygen. This make the compound a ketone. This means that we replace the -e ending on the "butane" with an -one ending to get butanone. (We could also use a 2- in front of this name to indicate that it is the 2nd carbon which is a member of the carbonyl group. This gives the name 2-butanone for this particular compound. However, the 2- is unnecessary here since if the carbonyl group were to be moved one carbon to the right we would start numbering from the right side of the compound and that carbon would be #2.) H H H | | | H-C-C-C-C-H | || | | H O H H butanone In this example I would also like to point out that the alcohol we start with, and the ketone we end up with both have the same number of carbon atoms. In addition, the carbonyl group in the ketone is in the same location as the hydroxyl group in the alcohol. This is a very important consideration when you are trying to make a particular ketone. You need Continue reading >>

Chapter 14 Aldehydes And Ketones

Chapter 14 Aldehydes And Ketones

Spencer L. Seager Michael R. Slabaugh www.cengage.com/chemistry/seager ALDEHYDES AND KETONES The carbonyl group: Aldehydes have at least one hydrogen attached to the carbonyl group. Ketones have two carbons attached to the carbonyl group. NAMING ALDEHYDES Find the longest carbon chain that contains the aldehyde group. Change ending of the root hydrocarbon name by dropping –e and adding –al. All other branches and groups are named and located using standard IUPAC system. Examples: 3-bromobutanal 2-ethylbutanal NAMING KETONES Find the longest chain that contains C=O. Using the root alkane name, drop the –e ending and change to –one. Number the longest carbon chain so the C=O group has the lowest number. Name and number other substituents as before. Examples: 3-methyl-2-pentanone 2-methylcyclohexanone ALDEHYDE AND KETONE REACTIONS (continued) The ease with which aldehydes are oxidized allows us to test for the presence of aldehydes with Tollens’ reagent or Benedict’s reagent. In general, ketones fail to react with these reagents. From left to right, three test tubes containing potassium dichromate (K2Cr2O7), acetone, and benzaldehyde. After the addition of equal amounts of K2Cr2O7, the acetone remains unreacted, whereas the benzaldehyde is oxidized. ALDEHYDE AND KETONE REACTIONS (continued) In the presence of aldehydes, Benedict’s reagent produces a red precipitate. From left to right, three test tubes containing Benedict’s reagent, 0.5% glucose solution, and 2.0% glucose solution. The addition of Benedict’s reagent from the first tube produces colors (due to the red Cu2O) that indicate the amount of glucose present. Continue reading >>

Organic Chemistry/ketones And Aldehydes

Organic Chemistry/ketones And Aldehydes

Aldehydes () and ketones () are both carbonyl compounds. They are organic compounds in which the carbonyl carbon is connected to C or H atoms on either side. An aldehyde has one or both vacancies of the carbonyl carbon satisfied by a H atom, while a ketone has both its vacancies satisfied by carbon. 3 Preparing Aldehydes and Ketones Ketones are named by replacing the -e in the alkane name with -one. The carbon chain is numbered so that the ketone carbon, called the carbonyl group, gets the lowest number. For example, would be named 2-butanone because the root structure is butane and the ketone group is on the number two carbon. Alternatively, functional class nomenclature of ketones is also recognized by IUPAC, which is done by naming the substituents attached to the carbonyl group in alphabetical order, ending with the word ketone. The above example of 2-butanone can also be named ethyl methyl ketone using this method. If two ketone groups are on the same structure, the ending -dione would be added to the alkane name, such as heptane-2,5-dione. Aldehydes replace the -e ending of an alkane with -al for an aldehyde. Since an aldehyde is always at the carbon that is numbered one, a number designation is not needed. For example, the aldehyde of pentane would simply be pentanal. The -CH=O group of aldehydes is known as a formyl group. When a formyl group is attached to a ring, the ring name is followed by the suffix "carbaldehyde". For example, a hexane ring with a formyl group is named cyclohexanecarbaldehyde. Aldehyde and ketone polarity is characterized by the high dipole moments of their carbonyl group, which makes them rather polar molecules. They are more polar than alkenes and ethers, though because they lack hydrogen, they cannot participate in hydrogen bonding like Continue reading >>

R-5.6.2 Ketones, Thioketones, And Their Analogues

R-5.6.2 Ketones, Thioketones, And Their Analogues

Specific Classes of Compounds R-5.6.2.1 Ketones. The generic term "ketone" refers to compounds containing a carbonyl group, >C=O, joined to two carbon atoms. Ketones are named substitutively by adding a suffix such as "-one", and "-dione" to the name of a parent hydride with elision of the final "e" of the parent hydride, if any, before "o". When a group having priority for citation as principal characteristic group is present, a ketone is described by the prefix "oxo-". Functional class names for monoketones and vicinal diketones, etc., are formed by citing the prefix names for the two groups attached to the carbonyl group(s) in alphabetical order followed by the class name "ketone", "diketone", etc., as a separate word. Examples to R-5.6.2.1 Diketones derived from cyclic parent hydrides having the maximum number of noncumulative double bonds by conversion of two -CH= groups into >CO groups with rearrangement of double bonds to a quinonoid structure may be named alternatively by adding the suffix "-quinone" to the name of the aromatic parent hydride. Example to R-5.6.2.1 Acyl derivatives of benzene or naphthalene have been named by changing the "-ic acid" or "-oic acid" ending of a trivial name of the acid corresponding to the acyl group to "-ophenone" or "-onaphthone". Only the names acetophenone, propiophenone, and benzophenone are retained in these recommendations (see R-9.1, Table 27(a)). Acyl derivatives of cyclic parent hydrides are named by prefixing the substituent name derived from the cyclic parent hydride to the name of the acyclic ketone. Example to R-5.6.2.1 Some trivial names are retained (see R-9.1, Table 27(a)). R-5.6.2.2 Chalcogen analogues of ketones are named by using suffixes such as "-thione" and "-selone", and prefix names such as "thioxo-" and "s Continue reading >>

More in ketosis