Chemistry

Ketones


Area of ​​Expertise - Organic chemistry

A ketone is a compound with a carbonyl group (C = O group) attached to two organic radicals.

The simplest ketone is acetone (propanone), a commonly used solvent.

See also: keto-enol tautomerism

Learning units in which the term is dealt with

Wittig reaction25 min.

ChemistryOrganic chemistryAlkenes

This learning unit is an introduction to the Wittig reaction (Wittig olefination) and related types of reactions.

Interpretation of C, H, O compounds60 min.

ChemistryAnalytical chemistryIR / Raman spectroscopy

This chapter includes the interpretation of IR and Raman spectra of the compounds that consist of carbon, hydrogen and oxygen. On the basis of important group frequencies, after working through this section, you should be able to differentiate between the individual substance classes.

Reactions of carboxylic acids45 min.

ChemistryOrganic chemistryCarboxylic acids

The learning unit describes the different reactions of carboxylic acids. On the one hand, attacks on the carboxy group and, on the other hand, reactions at the alpha carbon.

The Grignard reaction20 min.

ChemistryOrganic chemistryOrganometallic compounds

It is one of the classic organometallic reactions for building CC bonds in synthetic organic chemistry and, thanks to its wealth of variants, opens up the possibility of converting a large number of different functional groups into others - the Grignard reaction, which has not been used for over 100 years is to be imagined without the laboratories.

Meerwein-Ponndorf-Verley reduction20 min.

ChemistryOrganic chemistryReduction reactions

This learning unit explains the reaction principle of the Meerwein-Ponndorf-Verley reduction. Aldehydes and ketones can be reduced to the corresponding alcohol.

Aldehydes and ketones30 min.

ChemistryOrganic chemistryCarbonyl compounds

In this learning unit, the substance class of aldehydes and ketones is presented. The enormous importance of these compounds both in technology and in the form of natural substances is explained using examples. In addition, the presentation and the properties are discussed.


Aldehydes and ketones

Aldehydes and ketones are important classes of compounds in organic chemistry. The most important representatives are the alkanals and alkanones. The molecules of both substance classes contain the carbonyl group (-C = O) as a functional group.
Aldehydes and ketones show up, inter alia. through intense gossip. They are therefore used as fragrances and aromas. Both aldehydes and ketones can be reduced to alcohols. In contrast, only aldehydes can be easily oxidized, producing carboxylic acids.

Aldehydes and ketones

#Aldehyde #ketones #methanal #formaldehyde #acetone #propanone #ethanal #acetaldehyde #carbonyl #carbonyl group #carbonyl compounds #alkanals #alcanones #propanal #butanone #oxidation

Aldehydes and ketones are similar classes of compounds, which accordingly have similar chemical and physical properties. You can z. B. reduce well, are mostly volatile, flammable and often have a characteristic, intense odor. However, there are also differences: in contrast to aldehydes, ketones cannot be oxidized.

The similarities between the two substance classes can be explained by the similarity of the functional groups of the aldehydes and the ketones. Common to both is the -C = O group, which is also called the carbonyl group. In this functional group, the tetravalent (tetravalent) carbon atom, also known as the carbonyl carbon atom, is linked to an oxygen atom via a double bond. The two remaining bonding possibilities (valences) can be occupied with carbon or hydrogen atoms. This is exactly where aldehydes and ketones differ (see Figure 1).

In aldehydes n (at least) one of the two bonding possibilities (valences) is always occupied by a hydrogen atom. The functional group of the aldehydes (aldehyde group) is thus:

The remaining free valence (possibility of bonding) can carry any hydrocarbon radical. If the remainder is derived from the alkanes, the corresponding aldehyde is also known as an alkanal. The ending -al stands for the aldehyde group. The systematic name results from the name of the hydrocarbon with the ending -al. In addition, "trivial names" are often used.

In ketones n, both free valences of the carbonyl carbon atom are occupied by any hydrocarbon radicals. If the two hydrocarbon radicals are identical, one also speaks of symmetrical n ketones; if they are different, of asymmetrical (or asymmetrical) ketones. The functional group is called a keto group, which means a carbonyl group that carries two hydrocarbon radicals.

The ending -on indicates the presence of the keto group. The full name results from the designation for the hydrocarbon skeleton and the ending -on. For an exact description it is necessary to indicate the position of the keto group. This is done by inserting a number in front of the ending -on, which indicates the position. The numbering of the carbon atoms starts from the shorter side, so that the lowest possible numbers are required. Non-systematic names are also often used for ketones, whereby the two sides of the keto group are usually named individually.

formulaSurnamealternative names
Propan-2-oneDimethyl ketone / acetone
Butan-2-oneEthyl methyl ketone
Hexan-3-oneEthyl propyl ketone

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Reactions of aldehydes and ketones with chlorine and fluorosulfonyl isocyanate

Professor Werner Schultheis Dedicated to the 70th birthday.

Please direct correspondence to this author Search for more papers by this author

Farbwerke Hoechst AG, D-6230 Frankfurt (Main) 80

Farbwerke Hoechst AG, D-6230 Frankfurt (Main) 80

Farbwerke Hoechst AG, D-6230 Frankfurt (Main) 80

Professor Werner Schultheis Dedicated to the 70th birthday.

Please direct correspondence to this author Search for more papers by this author

Abstract

Chlorine and fluorosulfonyl isocyanate (1 a and b) react at low temperature with aldehydes in a molar ratio of 1: 2 to give the dioxazinones 2, with s-trioxane and 1,3,5,7-tetroxocane to give tetraoxaazacyclodecanone 6. The reaction with ketones takes place different depending on their structure. In special cases, methylene amino sulfohalides such as 9. N- (halosulfonyl) -β-ketocarboxamides such as 11. are usually formed with α-substitution Oxazinones 13. - β-Diketones add the halosulfonyl isocyanates 1 a and b to 17 at the oxygen at low temperatures, and to 18 at room temperature they are substituted at the α-carbon. The isobutanetriones 28 are obtained analogously from β-ketocarboxylic acids.

Abstract

Reactions of Aldehydes and Ketones with Chloro- and Fluorosulfonyl Isocyanate

At low temperatures, chloro- and fluorosulfonyl isocyanate (la or b) react with aldehydes at a molar ratio of 1: 2, to give derivatives of dioxazinone 2, and with s-trioxane and 1,3,5,7- tetroxocane, to give tetraoxaazacyclodecanones 6. With ketones the reaction course depends upon their structure in special cases it results in the formation of methyleneaminosulfohalides 9. Usually N-sulfohalides of F-keto carboxamides such as 11 are formed by substitution in the a-position. a, P-Unsaturated ketones yield oxazinones 13 by a (4 + 2) -cycloaddition reaction including participation of the CC bond. - At low temperatures, the halosulfonyl isocyanates 1 a and b add to the oxygen of P-diketones forming 17, whereas at room temperature they react at the z-carbon atom forming 18. In an analogous way, reaction with P-keto - carboxylic acid derivatives leads to formation of the isobutanetriones 28.