Functional groups, organic nitrile

Nitriles are organic compounds that contain a triple bond between a carbon and a nitrogen atom. The functional group in nitriles is the cyano (—C=N)... 

The production of optically active cyanohydrins, with nitrile and alcohol functional groups that can each be readily derivatized, is an increasingly significant organic synthesis method. Hydroxynitrile lyase (HNL) enzymes have been shown to be very effective biocatalysts for the formation of these compounds from a variety of aldehyde and aliphatic ketone starting materials.Recent work has also expanded the application of HNLs to the asymmetric production of cyanohydrins from aromatic ketones. In particular, commercially available preparations of these enzymes have been utilized for high ee (5)-cyanohydrin synthesis from phenylacetones with a variety of different aromatic substitutions (Figure 8.1). 

As particular types of vibration always occur at a similar wavenumber, it is possible to build up a table of characteristic absorptions. Such a table is given on p. 14 of the SQA Data Booklet. If you examine this table, you will see, for example, that an absorption in the wavenumber range 2260-2215 cm is indicative of a nitrile group and is due to stretching of the C=N bond. So, given the infrared spectrum of an unknown organic compound and a table of characteristic absorptions, it should be possible to identify the functional groups present in the compound. In most cases, however, more information is required to determine the full structure. 

Almost all organic functional groups except for olefinic double bonds are reduced by hthium aluminum hydride. It reduces acids, esters, acid chlorides, amides, imides, imines, nitriles, nitroorganics, epoxides, and lactones. 

The conjugate addition of heteronucleophiles to activated alkenes has been used very often in organic synthesis to prepare compounds with heteroatoms [3 to various activating functional groups, e.g. ketones, esters, nitriles, sulfones, sulfoxides and nitro groups. As in the Michael reaction, a catalytic amount of a weak base is usually used in these reactions (with amines as nucleophiles, no additional base is added). 

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