Carbonyl Compounds Lab Report

Preparing nitriles from carbonyl compounds is useful in reactions because nitriles are versatile functional groups1. Not only are they versatile functional groups but they serve as precursors in several transformations. The cyano-group is found in many bioactive molecules and plays a role in hydrogen bonding to certain biological receptors.4 Nitriles are carboxylic acid derivatives because they can easily be converted to carboxylic acid under either basic or acidic conditions. Piperonal is an aromatic compound that is present in vanilla, camphor wood, and olive leaves. It is typically used as a fragrance or a flavor.2 Piperonal also has the ability to inhibit foodborne pathogens and to improve hepatic insulin and ER stress response2. It does
The oxygen anion then attacks the hydrochloride portion to create an alcohol. The chloride ion attacks hydrogen in the hydroxylamine to create hydrochloric acid. The alcohol will then attack the HCl to create an oxygen cation. The lone pair on the hydroxylamine will attack the carbon, releasing water and creating a double bond between the nitrogen and carbon. The remaining hydrogen will be attached by a chloride ion to create the oxime intermediate. To create the desired product, the oxygen in the intermediate will attack the HCl that was formed making another oxygen cation and chloride ion. The Cl- will attack the hydrogen connected to the carbon of the double bond, forming the nitrile and expelling
The product was then purified by flash chromatography and analyzed by IR, 1H NMR and 13C NMR. The synthesis of piperonylontitrile was successful. There was a yield of a pale yellow crystal of 36%. The average recovery is 51% with there being a range from 0-94 %1. A reason for a smaller yield than notable reported could have been due to transfer of the product from glassware to glassware. Some may have been left behind. Another reasoning for a smaller yield could be due to the fact that as soon as the column was ran the product immediately eluted the column so a small amount was collected. Although this is a possible reason the desired product still formed. Column chromatography was chosen to purify the compound because it can purify almost any mixture of solids and/or liquids. Using a solvent mixture that was composed of 15% ethyl acetate in hexanes, the product eluted straight from the column. It was predicted that the starting material would elute first but there was none present when the column was ran. Since there was not much of a separation, what eluted from the column was analyze to confirm that it was the pure