Introduction: Alkyl halides are compounds that are considered as good “leaving groups” when these good leaving groups are replaced by another atom that is called “substitution”. When a nucleophile substitution occurs, this is an act of replacement of the leaving group [1]. When substitute happens nucleophile reacts, that is and electron pair donor, while the reaction releases this make electrophile as the receptor [2]. These alkyl halides will be prepare from alcohol while reacting with halides, this mechanism support the substitution of alcohols [3]. A “First order of Nucleophilic substitution” of SN1, a weak nucleophile, which is unimolecular, a reaction that occurs step by step. The solvent that is favored by SN1 is polar protic [4]. SN2, …show more content…
After 5 minutes yellow in color formed and precipitation did not form. Other steps in this experiment did not happen for test tube 1, for example, after the first 5 minutes, and no changes occurred test tube 1 needed to go into the ice bath to confirm “no reaction”. Therefore test tube 1 data were inconclusive. Test tube 2 contained the synthesized product along with 1 mL of 1% ethanolic silver nitrate, precipitation came rapidly fast for test tube 2. The color was clear and instantly cloudy and white precipitate appeared. Test tube 3 contained 0.2 mL of 1-chlorobutane and the tert-butyl chloride, when shaking the test with the product closed in by the cork the test tube products went from clear to dull yellow color. No precipitation was formed after 5 minutes; therefore, the test tube was placed in a 53 °C of water for an additional 5 minutes. Precipitation appear on the side of the test tube. Test tube 4 contained 0.2 mL of 1-chlorobutane and the tert-butyl chloride, no changes and no precipitation were form. Same as for test tube 1, test tube 4 did not undergo the ice bath after the first 5 minutes, the ice bath is used to confirm if reaction is possible. Test tube 4 data was also …show more content…
In the reaction involving both tert-butyl chloride and tert-butyl alcohol there were correctly synthesized. In SN1 as I mention in the introduction, is a weak nucleophile, unimolecular, and polar protic that most like occur in those leaving groups that is tertiary. In SN2, is a strong nucleophile, bimolecular and is polar aprotic and reaction for this leaving group is primary. In the last part of the experiment SN1 and SN2 reactions was analyzed when 18% of solution of sodium iodide and silver nitrate was mixed in the respective test tubes although test 1 form a yellow color; however, the lack of precipitation indicates this wouldn’t be consider a reaction so these data are inconclusive. Test tube 2 contained the synthesized product along with 1 mL of 1% ethanolic silver nitrate, precipitation came rapidly fast, and this came to be the most successful testing. Test tube 3 contained 0.2 mL of 1-chlorobutane and the tert-butyl chloride and had the positive reactions that was aimed for from the introduction were the ones that came out to be the most successful
The goal of this two week lab was to examine the stereochemistry of the oxidation-reduction interconversion of 4-tert-butylcyclohexanol and 4-tert-butylcyclohexanone. The purpose of first week was to explore the oxidation of an alcohol to a ketone and see how the reduction of the ketone will affect the stereoselectivity. The purpose of first week is to oxidize the alcohol, 4-tert-butylcyclohexanol, to ketone just so that it can be reduced back into the alcohol to see how OH will react. The purpose of second week was to reduce 4-tert-butylcyclohexanol from first week and determine the effect of the product's diastereoselectivity by performing reduction procedures using sodium borohydride The chemicals for this lab are sodium hypochlorite, 4-tert-butylcyclohexanone
Triphenylmethyl Bromide. A 400 mL beaker was filled with hot water from the tap. Acetic acid (4 mL) and solid triphenylmethanol (0.199 g, 0.764 mmol) were added to a reaction tube, with 33% hydrobromic acid solution (0.6 mL) being added dropwise via syringe. The compound in the tube then took on a light yellow color. The tube was then placed in the beaker and heated for 5 minutes. After the allotted time, the tube was removed from the hot water bath and allowed to cool to room temperature. In the meantime, an ice bath was made utilizing the 600 mL plastic beaker, which the tube was then placed in for 10 minutes. The compound was then vacuum filtered with the crystals rinsed with water and a small amount of hexane. The crude product was then weighed and recrystallized with hexane to form fine white crystals, which was triphenylmethyl bromide (0.105 g, 0.325 mmol, 42.5%). A Beilstein test was conducted, and the crystals produced a green to greenish-blue flame.
This experiment was divided into two main steps. The first step was the addition of bromine to trans-stilbene. Trans-stilbene was weighted out 2.00g, 0.0111mol and mixed with 40ml of glacial acetic acid in 100ml Erlenmeyer flask on a hot bath. Pyridinium hydrobromide perbromide of 4.00g, 0.0125mol was added carefully into the flask.
The most classic and standard procedure for producing esters is the Fisher-esterification reaction. Discovered in 1895 by German chemists Emil Fischer and Arthur Speier 4, this reaction involves refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst. In order to drive the equilibrium towards the products, the water from the dehydration process must be removed and there must be an excess amount of alcohol. A vast range of carboxylic acids may be used for this reaction however the type of alcohols are limited. Primary and secondary alcohols are most frequently used in esterification reactions, tertiary alcohols are steric ally hindered usually resulting in poor yields5 and tend to undergo elimination reactions instead. In this rea...
The reaction performed in this experiment was bromination of an alkene, using trans-Cinnamic acid, Pyridinium Tribromide, and Glacial Acetic Acid.
The goal of this lab is to synthesize maleic anhydride with polyethylene glycol of 200g/mol molecular weight (PEG 200) and 2,3-dimethyl-1,3-butadiene to get 4,5-dimethylcyclohexane-1,2-dicarboxylic acid anhydride and its diacid by using Diels-Alders reaction and hydrolysis, respectively. The crystals were determined using melting point determination and IR spectroscopy.
Procedure: Anisole (0.35mL, 0.0378mol) was obtained and placed in a pre-weighed 25 mL round bottom flask, along with 2.5 mL of glacial acetic acid and a magnetic stir bar. Then the reaction apparatus was assembled, the dry tube was charged with conc. sodium bi sulfate, the 25 mL round bottom was attached to the apparatus, and 5 mL of Br2/HBr mixture was obtained and placed in the round bottom. The reaction took place for 20 minutes. An orange liquid was obtained and placed in a 125 mL Erlenmeyer flask along with 25 mL of water and 2.5 mL of conc. Sodium bisulfate soln. The solution was then placed in an ice bath to precipitate and then the solid product was filter in a Buchner funnel. These crystals were then re-dissolved minimum amount of hot solvent (heptane) and recrystallized. Once a dry product was obtained, a melting point was established (2,4-Dibromoanisol mp 55-58 C) and percent yield was established (52%).
In this lab 4-tert-butylcyclohexanone is reduced by sodium borohydride (NaBH4) to produce the cis and trans isomers of 4-tert-butylcyclohexanol. Since the starting material is a ketone, NaBH4 is strong enough to perform a reduction and lithium aluminum hydride is not needed. NaBH4 can attack the carbonyl group at an equatorial (cis) or axial (trans) position, making this reaction stereoselective. After the ketone is reduced by the metal-hydride, hydrochloric acid adds a proton to the negatively charged oxygen to make a hydroxyl group. The trans isomer is more abundant than the cis based on the results found in the experiment and the fact that the trans isomer is more stable; due to having the largest functional groups in equatorial positions.
The reaction of (-)-α-phellandrene, 1, and maleic anhydride, 2, gave a Diels-Alder adduct, 4,7-ethanoisobenzofuran-1,3-dione, 3a,4,7,7a-tetrahydro-5-methyl-8-(1-methylethyl), 3, this reaction gave white crystals in a yield of 2.64 g (37.56%). Both hydrogen and carbon NMR as well as NOESY, COSY and HSQC spectrum were used to prove that 3 had formed. These spectroscopic techniques also aided in the identification of whether the process was attack via the top of bottom face, as well as if this reaction was via the endo or exo process. These possible attacks give rise to four possible products, however, in reality due to steric interactions and electronics only one product is formed.
The competing enantioselective conversion method uses each enantiomer of a kinetic resolution reagent, in this case R-HBTM and S-HBTM, in separate and parallel reactions, where the stereochemistry of the secondary alcohol is determined by the rate of the reactions. When using the CEC method, the enantiomer of the secondary alcohol will react with one enantiomer of the HBTM acyl-transfer catalyst faster than with the other HBTM enantiomer. The mnemonic that identifies the absolute configuration of the secondary alcohol is as follows: if the reaction is faster with the S-HBTM, then the secondary alcohol has the R-configuration. In contrast, if the reaction is faster with the R-HBTM, then the secondary alcohol has the S-configuration. Thin layer chromatography will be used to discover which enantiomer of HBTM reacts faster with the unknown secondary alcohol. The fast reaction corresponds to a higher Rf spot (the ester) with a greater density and a slower reaction corresponds to a lower Rf spot with high de...
Reacting 1-butanol produced 2-trans-butene as the major product. 1-butanol produces three different products instead of the predicted one because of carbocation rearrangement. Because of the presence of a strong acid this reaction will undergo E1 Saytzeff, which produces the more substituted
The purpose of this lab was to perform an electro-philic aromatic substitution and determine the identity of the major product. TLC was used to detect unre-acted starting material or isomeric products present in the reaction mixture.
Then the reaction tube was capped but not tightly. The tube then was placed in a sand bath reflux to heat it until a brown color was formed. Then the tube was taken out of the sand bath and allowed to cool to room temperature. Then the tube was shaken until a formation of a white solid at the bottom of the tube. After formation of the white solid, diphenyl ether (2 mL) was added to the solution and heated until the white solid was completely dissolved in the solution. After heating, the tube was cooled to room temperature. Then toluene (2 mL) was added to the solution. The tube was then placed in an ice bath. Then the solution was filtered via vacuum filtration, and there was a formation of a white solid. Then the product was dried and weighed. The Final product was hexaphenylbenzene (0.094 g, 0.176 mmol,
Substrate 1 and 2 both formed turbidity, although substrate 2 reacted faster because it is a better leaving group due to its increased size. Substrate 8 occurred immediately although it is only a secondary bromine due to bromine being such a good leaving group as well as because the silver acts as a great catalyst. Substrate 3 did not react due to the lack stability in terms of surrounding steric
The product was recrystallized to purify it and the unknown filtrate and nucleophile was determined by taking the melting points and performing TLC. Nucleophilic substitution reactions have a nucleophile (electron pair donor) and an sp3 electrophile (electron pair acceptor) with an attached leaving group. This experiment was a Williamson ether synthesis usually SN2, with an alkoxide and an alkyl halide. Conditions are favored with a strong nucleophile, good leaving group, and a polar aprotic solvent.