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Published by: Myrrh Oliver Casinabe on Jun 22, 2012
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Nitriles
Suffix: -nitrile or -onitrilePrefix: cyano-
Nitriles contain a carbon - nitrogen triple bond (R-C
N or R-CN). They are indirectly related toamides (by the loss of H
2
O from a primary amide), and react chemically similar to carboxylicacids and their derivatives. It should be noted that H-C
N is not truly a nitrile and is namedhydrogen cyanide.When a nitrile group is the highest priority functional group present in the molecule, it is namedas an
 alkanenitrile
(alkenenitrile, alkynenitrile, ...). Since the -C
N must occur at the end of achain of carbon atoms, the carbon of the nitrile will be carbon 1 in the numbering scheme. Otherfunctional groups are located by this numbering scheme. Since the nitrile group is always atcarbon number 1, there is no need to indicate its' location.Examples naming simple nitriles:
Compound Name
 
Line Drawing
 
3D Model
 ethanenitrilepropanenitrilebutanenitrile2-methylpropanenitrilecyclobutyronitrile *pentanedinitrile *** note: the -yl is changed to a -yro.** note: numbers are not needed as the nitriles must be at the ends of the chain.Examples naming more complex nitriles:
 
Compound Name
 
Line Drawing
 4,4-dimethylpentanenitrile2,4-pentadienenitrile4-amino-3-hydroxy-2-methylhexanenitrile4-chloro-2-cyclohexenenitrile2-mercapto-4-oxo-6-heptynenitrile
Nitriles as Substituents:
In more complex molecules with higher priority functional groups the nitrile group is named as a
 cyano-
substituent. It is located by numbering the longest chain of carbons (according to thehigher priority functional group) and locating the carbon atom to which the -CN group isattached by this numbering scheme. Examples of these structures will be given in the subsequentpages.
Acetonitrile
3
CN. This colourless liquid is thesimplest organic nitrile.It is produced mainly as a byproduct of  acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of  butadiene.
 In the laboratory, it is used as a medium-polarity solvent that is miscible with water and has a convenient liquid range. With a dipole moment of 3.92 D
[
]
, acetonitrile dissolves awide range of ionic and nonpolar compounds (e.g. Wohl-Ziegler reaction)and is useful as a mobile phase in HPLC and LCMS.
 
Contents
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[edit] Applications
Acetonitrile is used mainly as a solvent in the purification of  butadiene in refineries. It is widely used in battery applications because of its relatively high dielectric constant and ability to dissolve electrolytes. For similar reasons it is a popular solvent in cyclic voltammetry.  Its low viscosity and low chemical reactivity make it a popular choice for liquid chromatography. Acetonitrile plays a significant role as the dominant solvent used in the manufacture of DNAoligonucleotides from monomers.  Industrially, it is used as a solvent for the manufacture of  pharmaceuticals and photographic film.
[edit ]Organic synthesis
Acetonitrile is a common two-carbon building block in organic synthesis
 of many usefulchemicals, including acetophene, thiamine, acetamidine,and 
[edit ]Ligand in coordination chemistry
In inorganic chemistry,acetonitrile is employed as a solvent and often an easily displaceable ligand.For example, PdCl
2
(CH
3
CN)
2
is prepared by heating a suspension of (polymeric)palladium chloride in acetonitrile:
PdCl
2
+ 2 CH
3
CN → PdCl
2
(CH
3
CN)
2
 

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