The Synthesis Of 13 Butadienes

The objective of this lab was to create a ketone through an oxidation reaction using a using a secondary alcohol and oxidizing agent in order to use that ketone in a reduction reaction with a specific reducing agent to determine the affect of that reducing agent on the diastereoselectivity of the product. In the first part of this experiment, 4-tert-butylcyclohexanol was reacted with NaOCl, an oxidizing agent, and acetic acid to form 4-tert-butylcyclohexanone. In the second part of this experiment, 4-tert-butylcyclohexanone was reacted with a reducing agent, either NaBH4 in EtOH or Al(OiPr)3 in iPrOH, to form the product 4-tert-butylcyclohexanol. 1H NMR spectroscopy was used to determine the cis:trans ratio of the OH relative to the tert-butyl group in the product formed from the reduction reaction with each reducing agent. Thin-layer chromatography was used in both the oxidation and reduction steps to ensure that each reaction ran to completion.

Discussion: In the synthesis of 1-bromobutane alcohol is a poor leaving group; this problem is fixed by converting the OH group into H2O, which is a better leaving group. Depending on the structure of the alcohol it may undergo SN1 or SN2. Primary alky halides undergo SN2 reactions. 1- bromobutane is a primary alkyl halide, and may be synthesized by the acid-mediated reaction of a 1-butonaol with a bromide ion as a nucleophile. The proposed mechanism involves the initial formation of HBr in situ, the protonation of the alcohol by HBr, and the nucleophilic displacement by Br- to give the 1-bromobutane. In the reaction once the salts are dissolved and the mixture is gently heated with a reflux a noticeable reaction occurs with the development of two layers. When the distillation was clear the head temperature was around 115oC because the increased boiling point is caused by co-distillation of sulfuric acid and hydrobromic acid with water. When transferring allof the crude 1-bromobutane without the drying agent,

In the controlled oxidation reactions of 1-butanol and 2-butanol with KMnO4, there is also a formation of water. The primary alcohol 1-butanol, reacted with KMnO4 to create butanal, an aldehyde, and water as products. Also the secondary alcohol, 2-butanol and KMnO4

The Hydroxyl group on alcohols relates to their reactivity. This concept was explored by answering the question “Does each alcohol undergo halogenation and controlled oxidation?” . Using three isomers of butanol; the primary 1-butanol, the secondary 2-butanol and the tertiary 2-methyl-2-propanol, also referred to as T-butanol, two experiments were performed to test the capabilities of the alcohols. When mixed with hydrochloric acid in a glass test tube, the primary alcohol and secondary alcohols were expected to halogenate, however the secondary and tertiary ended up doing so. This may have been because of the orientation of the Hydroxyl group when butanol is in a different

The synthesis of the alkyl halide n-Butyl Bromide from alcohol is the foundation for the experiment. During the isolation of the n-butyl bromide, the crude product is washed with sulfuric acid, water, and sodium bicarbonate to remove any remaining acid or n-butyl alcohol. The primary alkyl halide halide n-butyl bromide is prepared by allowing n-butyl alcohol to react with sodium bromide and sulfuric acid. The sodium bromide reacts with sulfuric acid to produce hydrobromic acid . Excess sulfuric acid acts to shift the equilibrium and speed up the reaction by producing a higher concentration of hydrobromic acid. The

9-anthraldehyde and (carbethoxymethylene)triphenylphosphorane were reacted together using the Wittig reaction to produce E-3-(9-Anthryl)-2-propenoic acid ethyl ester. .100 g of 9-anthraldehyde and .180 g of (carbethoxymethylene)triphenylphosphorane were used. 9-anthraldehyde was a green powder while (carbethoxymethylene)triphenylphosphorane was a white powder. Both were added together into a 3.00 mL conical vial with a magnetic spin valve. The vial was inserted into a 120 C sand bath to melt the reagents. Once the reagents melted, they were stirred for 15 minutes (2:30 pm-2:45 pm). After stirring, the vial was removed to cool to room temperature. 3.00 mL of hexanes were added to the vial and the suspension was stirred. The solvent was removed

The Diels-Alder reaction was discovered and named after the Nobel Prize winning scientists Kurt Alder and Otto Diels in 1928. Such a reaction occurs when a diene with two adjacent double bonds is mixed with a dienophile consisting of a double bond in order to create a cyclohexene. The diene must be in the s-cis conformation in order for the electron transfer to engage correctly. If the diene in question is in s-trans conformation then the access to the molecules is limited, thus, no reaction can occur. The dienophile we used was maleic anhydride. Maleic anhydride possesses high electron withdrawing characteristics which caused a very quick reaction. The reaction will

The purpose of this experiment is to synthesize 1-bromobutane from 1-butanol and sodium bromide. In order for this reaction to reach completion there are four major operations that need to be performed. The four major operations include refluxing, simple distillation, separation, and drying.

After 10 minutes the reaction liquid was separated from the solid using a vacuum filtration system and toluene. The product was stored and dried until week 2 of the experiment. The product was weighed to be 0.31 g. Percent yield was calculated to be 38.75%. IR spectra data was conducted for the two starting materials and of the product. Melting point determination was performed on the product and proton NMR spectrum was given. The IR spectrum revealed peaks at 1720 cm-1, which indicated the presence of a lactone group, and 1730 cm-1, representing a functional group of a carboxylic acid (C=O), and 3300cm-1, indicating the presence of an alcohol group (O-H). All three peaks correspond with the desired product. A second TLC using the same mobile and stationary phase as the first was performed and revealed Rf Values of 0.17 and 0.43for the product. The first value was unique to the product indicating that the Diels-Alder reaction was successful. The other Rf value of 0.43 matched that of maleic anhydride indicating some

The purpose of this experiment is to convert carbonyl compounds to alkenes using Wittig reaction. In this case we will be synthesizing Trans-9-(2-phenylethenyl) anthracene from benzyltriphenylphosphonium chloride and 9-anthraldehyde. We will also aim to obtaining a high percent yield and purity for the synthesis of Trans-9-(2-phenylethenyl) anthracene. The mechanism for this reaction goes thus:

The dehydration of 2-methyl-2-butanol was performed using sulfuric acid and phosphoric acid in order to synthesize alkene products 2-methyl-1-butene and 2-methyl-2-butene. After carrying out steam distillation to isolate the organic alkenes from aqueous components within the reaction mixture, the purity and characterization of the products were then assessed through various analytical methods including Gas Chromatography (GC), Infrared Radiation (IR) Spectroscopy, and Nuclear Magnetic Resonance (NMR) Imaging. Through the characterization of the final products, it was found that little impurities remained in the final reaction solution and according to the GC, no alcohol remained in the vial after the reaction was complete. The actual yield

The aim of this experiment was to perform a reaction via a Sn1 reaction to prepare tert-Butyl chloride and test the effectiveness of the reaction by examining the reactivity of the product. To prepare tert-Butylchloride from tert-Butylalcohol, one must cause a Sn1 reaction to occur. An Sn1 reaction is a monomolecular nucleophilic substitution reaction, meaning that one molecule is involved in each step of the Sn1 reaction. First, the leaving group leaves. After the leaving group leaves, the nucleophile has enough room to form a bond with the carbocation.

For the identification of the product, IR, 13C NMR and 1H NMR spectra were examined, and the product was found to be butyl propionate. In the IR spectrum, RM-11-Bi, five key peaks are observed. These peaks are sp3 hybridized carbons at 2961 cm-1 and 2877 cm-1, an ester at 1737 cm-1, a

The purpose of this experiment was to perform a wittig reaction, the horner-emmons wittig specifically, reacting an aldehyde with an ylide to make an alkene. This particular variation of the wittig reaction has several advantages: It gives only the trans product; it uses a much milder base that is easier to handle; and it gives a water soluble byproduct which is easy to separate from the product. The reason that these advantages occur is a change in the structure of the ylide. Instead of a tripheylphosphine ylide, we use a diethylphosphonate ylide. The protons are much more acidic and its byproduct is negatively charged.

The objective of this experiment is to successfully perform a dehydration of 1-butanol and 2-butanol, also dehydrobromination of 1-bromobutane and 2-bromobutane to form the alkene products 1-butene, trans-2-butene, and cis-2-butene. The dehydration reactions react under and acid-catalysis which follows an E1 mechanism. It was found that dehydration of 1-butanol yielded 3.84% cis-2-butene, 81.83% trans-2-butene, and 14.33% 1-butene, while 2-butanol is unknown due to mechanical issues with the GC machine. For the dehydrobromination, with the addition of a