Cyclohexanone oxime
Encyclopedia
This page was incorrectly redirected to Caprolactam
Caprolactam
Caprolactam is an organic compound with the formula 5CNH. This colourless solid is a lactam or a cyclic amide of caproic acid. Approximately 2 billion kilograms are produced annually...

 (registry number 105-60-2).

Cyclohexanone oxime (registry number 100-64-1) is a different compound; both have the empirical formula C6H11NO, but are structural isomers of each other.

As the name implies, cyclohexanone oxime is a 6 membered ring, with a double bond to an oxime
Oxime
An oxime is a chemical compound belonging to the imines, with the general formula R1R2C=NOH, where R1 is an organic side chain and R2 may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds...

 group (=N-OH) (this replaces the double bond to an oxygen group seen in cyclohexanone).

Caprolactam is analogous to cyclohexanone with the NH group inserted into the ring, creating a 7 membered ring with a double bond to an oxygen side group adjacent to the NH group.

Caprolactam can be produce from cyclohexanone, by producing it's oxime and rearrangement to Caprolactam, an example of Beckmann rearrangement
Beckmann rearrangement
The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann , is an acid-catalyzed rearrangement of an oxime to an amide...

.
The source of this article is wikipedia, the free encyclopedia.  The text of this article is licensed under the GFDL.
 
x
OK