Oxa-Spengler Reaction Lab Report

Abstract – Methyl trans-cinnamate is an ester that contributes to the aroma of strawberry. It can be synthesized by an acid-catalyzed Fischer esterification of a methanol and trans-cinnamic acid under reflux. The solution was extracted to obtain the organic product, and evaporated residual solvent The yield was 68%, but there is some conflicting data regarding the purity. The melting point, IR, GC-MS indicate a highly pure desired product whereas 1H NMR shows there are unreacted reagents still present.

The purpose of this experiment is to perform a two step reductive amination using o-vanillin with p-toluidine to synthesize an imine derivative. In this experiment, 0.386 g of o-vanillin and 0.276 g of p-toluidine were mixed into an Erlenmeyer flask. The o-vanillin turned from a green powder to orange layer as it mixed with p-toludine, which was originally a white solid. Ethanol was added as a solvent for this reaction. Sodium borohydride was added in slow portion as the reducing agent, dissolving the precipitate into a yellowish lime solution. Glacial acetic acid and acetic anhydride were added to the mixture while refluxing, which converted the lime colored solution into a clear mixture. The flask was cooled in an ice bath and the solution

The formation of new carbon-carbon bonds is of central importance in organic chemistry and a prerequisite for all life on earth. Through the assembly of carbon atoms into chains, complex molecules, e.g. molecules of life, can be created. The importance of the synthesis of carbon-carbon bonds is reflected by the fact that Nobel Prizes in Chemistry have been given to this area many times: the Grignard reaction (1912), the Diels-Alder reaction (1950), the Wittig reaction (1979), and olefin metathesis to Y. Chauvin, R. H. Grubbs, and R. R. Schrock (2005) and Richard F. Heck , Ei-ichi Negishi, Akira Suzuki (2010) for the development of methods for palladium-catalyzed formation of carbon-carbon

The purpose of this experiment is to undergo bromination reaction of acetanilide and aniline to form 4-bromoacetanilide and 2,4,6-tribromoaniline respectively. Since -NHCOCH3 of acetanilide and -NH2 of aniline are electron donating groups, they are ortho/para directors due to resonance stabilized structure. Even though the electron donating groups activate the benzene ring, their reactivities are different and result in the formation of different products during bromination. In acetanilide, the lone pair of the nitrogen is delocalized into the

5-aminotetrazole monohydrate: In a 250 ml round-bottom flask equipped with a condenser for refluxing (90 °C) and a magnetic stirring bar, 5.00 g (5.95 mmol) dicyandiamide (three times crystallized), 7.47 g (11.9 mmol) sodium azide and 11.00 g (17.8 mmol) boric acid and 100 ml of water is added and allowed to reflux for 24 hours, after the completion of the reaction, until the solution pH to about 2 to 3 as hydrochloric acid 37% is added (about 12 ml) Then the reaction mixture was cooled in a refrigerator for 18 hours and the white crystals formed. The mixture was filtered and washed three times with 10 ml of water and and dried in 60 °C for 5 hours and finally 45.8 g of product by it will be obtained.

The purpose of this experiment was to identify the unknown alkyl bromide and ketone using a Grignard reaction and IR spectrum. Also, retrosynthesis analysis was used to determine the success of identifying starting material. The organometallic compounds have a carbon-metal bond that is used to create alcohol and to expand chains of carbons. Grignard reagents, a part of organometallic ionic compounds, are widely used in organic synthesis because they are considered strong base, strong base carbon nucleophile, and soluble in many organic solvents.

Sphingolipids encompass a complex range of membrane lipids in which a fatty acid is linked to a long sphingosine carbon backbone, primarily C18-sphinganine (18:0) and C18-sphingosine (C18:1) in mammals. Figure 1 shows a schematic representation of the sphingolipid metabolic pathway. Ceramide is central in sphingolipid metabolism and is produced by de novo and recycling pathways.37 In de novo synthesis, serine and palmitoyl-CoA are substrates of serine palmitoyl-transferase (SPT), the rate limiting enzyme that generates ketosphinganine (bottom). Ketosphinganine is reduced to form sphinganine, which is then N-acylated with fatty acids of different chain lengths by ceramide synthases (CerS), producing dihydroceramides.

The Diels-Alder reaction has been an area of great research interest with regards to enhancing enantioselectivity in the reaction by use of various catalysts and reaction conditions.

Week 1 a simple condensation reaction between benzaldeyde and hydroxylamine produced the product benzaldehyde oxime that was found to be in oil. The percentage yield of the experiment is 64%. The 36% loss can be due to the solution needing to be neutralised with glacial acid, there was no way to tell if the reaction was neutralised, to help increase yield the use of pH indictor paper to indicate whether the reaction was neutralised. As by using a rotary evaporator to remove the organic solvent may have caused small amounts of the product to evaporate off as it a low melting point solid, if the water bath temperature was too high would have caused to melt and evaporate off. As melting point was not measured was unable to tell whether the product is pure.

Dr. Condeiu’s presentation on synthetic organic chemistry was a rewarding experience because he touched on some very important concepts. Not only did he mention many of the things discussed in class in terms of real world examples, but he also brought a human face to being a synthetic organic chemist, and also mentioned several examples of synthetic challenges he has personally faced.

The Wittig reaction is valuable reaction. It has unique properties that allows for a carbon=carbon double bond to form from where a C=O double bond used to be located. Creating additional C=C double bonds is valuable due to its use in synthesis. The Wittig reaction will allow the synthesis of Stilbene (E and Z) from a Benzaldehyde (Ketcha, 141).

The objective of this experiment was to use an aldol condensation reaction to synthesize 3-nitrochalcone from 3- nitrobenzaldehyde. This was accomplished with a Diels-Alder reaction that utilized 3-nitrobenzaldehyde, acetophenone, ethanol, and sodium hydroxide.

There are several different reactions that can be used to synthesize an alkene product, however the main reaction being utilized for this experiment is the Wittig reaction and the Horner-Wadsworth-Emmons modification. The Wittig reaction involves a reaction between an aldehyde or ketone and ylid, which is also referred to as the Wittig reagent. The Wittig reagent is synthesized from a phosphonium salt and a strong base (Wittig Reaction, 2006). The reaction between the Wittig reagent and the ketone or aldehyde is a nucleophilic substitution; the carbon double bonded to the oxygen in the carbonyl is replaced with a carbon double bonded to another carbon (University of Liverpool, 2008).

Enzymes are biological catalyst that alters the chemical reaction rate without itself being altered which reacts with the substrate and converts the enzyme substrate complex into different molecules – product. Enzyme plays the consequential role in functioning of life process such as for growth, digestion of nutrients, excretion of metabolic waste, energy provider to brain and muscles and thus directly or indirectly involved in every biological processing of life. Apart from numerous life functioning role, enzymes are also used in industry-oriented procedure such as for drug delivery in biomedical research, production of biodiesel in energy sector, production of jams and syrups in food industry, treatment of sewage in waste management

Isoxazoline are five member heterocyclic compound. isoxazole and their derivatives have received much attention because of their wide application in medicine and pesticide chemistry. Many isoxazole compound including oxacillin sulfamethoxazole have been developed as pesticides and drugs. Isoxazoline derivative synthesized by various ways [1-2].