A total of 1.91 g of purified benzil was produced from this reaction which contained an observed melting point of 89-92 °C and a 77% yield. 13C NMR (CDCl3, 75Hz) δ: 175.8, 141.4, 128.3, 128.2, 127.4, 82.0 ppm. ScienceDirect ® is a registered trademark of Elsevier B.V. ScienceDirect ® is a registered trademark of Elsevier B.V. An IR spectrum was provided by PerkinElmer UATR Two Spectrophotometer. Stephen reaction is also known as Stephen aldehyde synthesis as the end product of this reaction is aldehydes. Copyright © 2015 Elsevier Ltd. All rights reserved. Supporting information IR, 1H NMR and 13C NMR spectra of benzil, benzoin, and benzilic acid are attached. It was all about Stephen reaction and its mechanism, if you are looking for more methods of preparation of aldehydes or other name reactions then register yourself on Vedantu.com or download Vedantu learning app for class 6-10, IITJEE and NEET. 1H NMR (CDCl3, 300 MHz) δ: 7.79 (d, J=1.5, 2H) 7.25 (m, 2H), 7.24 (m, 2H), 7.19 (m, 2H), 7.14 (m, 2H), 5.82 (d, J= 1.2, 1H), 3.92 (s, 1H) ppm. The crystals were isolated through vacuum filtration and washed with 4-mL portions of cold 95% ethanol. As Sn +2 changes into Sn +4 two electrons are released. The ylide is the regenerated catalyst and performs the mechanism again. After heating and magnetically stirring, the mixture was added to 40 mL of cool water and stirred until crystallized into a yellow solid. This appeared to be less than the ideal melting point of 95 °C, which could account for the lack of purity. As the second step of the multistep synthesis, the alcohol group of benzoin must be oxidized. We get ammonium chloride or ammonia also as a byproduct. For Enquiry. available on Vedantu website. 1H NMR (CDCl3, 300 MHz) δ: 7.86 (m, 4H), 7.56 (m, 2H), 7.53 (m, 4H) ppm. Henry Stephen is an English chemist. convert benzonitrile to benzaldehyde - Chemistry - TopperLearning.com | a2l5t49qq. The composition of the reaction mixture was analyzed by GC–MS. Reaction is given below –. For screening the pathway of benzyl alcohol conversion to benzonitrile the reaction was run at a large GHSV of 2838 h −1 (Table 5, entry 10). The IR and 1H NMR data displayed peaks that allowed for the distinction and identification of the different products that led to the ultimate synthesis of benzilic acid. The solution was cooled in an ice bath and the crystals were filtered through vacuum filtration and washed with 2, 30-mL portions of ice-cold water. If you are at an office or shared network, you can ask the network administrator to run a scan across the network looking for misconfigured or infected devices. Through recrystallization, a pure product of 2.07 g was collected, which produced a 44% yield. Stephen reaction is used for production of aldehydes by using alkyl cyanides. Advantages imply the production of ideal, marketable end products, and the synthesis of compounds that otherwise could not be produced through a simple reaction. 1H NMR (CDCl3, 300 MHz) δ: 7.47 (m, 6H), 7.26 (s, 4H), 2.18 (s, 1H) ppm. Contact. Aqueous sodium hydroxide (4.5 mL) was added and swirled until the solution appeared pale yellow. © 2016 Elsevier B.V. All rights reserved. In the process ammonia is released as by product. A peak at 2.18 ppm represented the hydrogen of the alcohol group. In cyanide group nitrogen is more electronegative than carbon. The remaining crystals were identified by the following properties: 0.41 g (17.4% yield) mp: 151-152 °C (lit: 150 °C). Disadvantages include time-consuming experiments, error within intermediate steps, or the presence of side reactions. The crystals were washed with 5-mL portions of ice-cold water and left to dry. The first reaction produced benzoin by using the thiamine hydrochloride catalyst, followed by an oxidation reaction to produce benzil, and a rearrangement to synthesize benzilic acid. Through the interaction with other molecules, the rearrangement characteristics of benzil have been proven based on the intramolecular oxidation and reduction forces of gaining and losing electrons.3 Overall, the combination of the various organic characteristics and experiments allow for the success of a multistep synthesis reaction.