To perform SN1 Reactions using triphenylmethanol to yield triphenylmethyl bromide and triphenylmethyl methyl ether Experimental Section Triphenylmethyl bromide. First, a hot water bath was prepared in a 400 mL beaker with a boiling stick and this was placed on the hot plate. Also, an ice bath was prepared in the 600 mL plastic beaker. Next, methanol (3.00 mL) was added to a small reaction tube and this was placed in the prepared ice bath, which was set aside for the second reaction. In another small reaction tube, triphenylmethanol (0.200 g, 0.776 mmol) was added and followed by acetic acid (4 mL). After this, a syringe and needle was used to add 33% hydrobromic acid (0.60 mL, 0.27 g, 3.3 mmol) dropwise to the reaction tube. Furthermore, swirled the reaction tube when 33% hydrobromic acid (0.60 mL, 0.27 g, …show more content…
Then, the reaction tube was lightly capped and the reaction tube was placed into the hot water bath for 5 min. The color of the reaction tube with triphenylmethanol (0.200 g, 0.776 mmol), acetic acid (4 mL), and 33% hydrobromic acid (0.60 mL, 0.27 g, 3.3 mmol) was a darker orange-yellow color in the beginning of the reaction. After, this reaction tube was heated in the hot bath for 5 min, the color changed from darker orange-yellow to a lighter orange-yellow color. After all of the triphenylmethanol (0.200 g, 0.776 mmol)
The objective of this laboratory experiment is to study both SN1 and SN2 reactions. The first part of the lab focuses on synthesizing 1-bromobutane from 1-butanol by using an SN2 mechanism. The obtained product will then be analyzed using infrared spectroscopy and refractive index. The second part of the lab concentrates on how different factors influence the rate of SN1 reactions. The factors that will be examined are the leaving group, Br versus Cl-; the structure of the alkyl group, 3◦ versus 2◦; and the polarity of the solvent, 40 percent 2-propanol versus 60 percent 2-propanol.
(Q4:SN2 Rxn) SN2 reactions occur when a primary alkyl halide (benzyl bromide – electrophile) is made to react with a nucleophile (the unknown reactant) in a strong base solution (sodium hydroxide). The hydroxide anion from the strong base can also act as a strong nucleophile which allows for the deprotonation of the unknown thereby leaving the unknown’s oxygen with a negative charge. The deprotonation of the unknown allows for the formation of a water molecule. The bromide in the benzyl bromide is a great leaving group
Using SN1 reaction mechanism with hydrochloric acid, t-Pentyl alcohol was converted to t-Pentyl chloride in an acid catalyzed reaction. The reaction took place in a separatory funnel designed to separate immiscible liquids. The crude product was extracted by transferring a solute from one solvent to another. The process of washing the solutions by phase transfer was used in order to remove impurities from the main solvent layer. Finally, the crude product was dried with anhydrous Calcium chloride and purified once more by simple distillation technique.
The reaction began with the insertion of magnesium into the carbon-bromine bond to generate the Grignard reagent. 96 mg of magnesium turnings were ground up with a mortar and pestle in order to remove any surface oxides and contaminations that may preclude magnesium’s ability to react with unreactive alkyl halides. The magnesium turnings, along with a small crystal of iodine and a drop of 1,2-dibromoethane were added to a round bottom flask. The 1,2-dibromoethane is necessary to activate the alkyl halide. In a conical vial 2mL of anhydrous ether
1 and 2) In this experiment, Sn2 nucelophilic substitution between an unknown nucleophile solution and the known reagents benzyl bromide and NaOH occurred to form a benzyl ether product. 3) Refluxing, recrystallization, melting point, and TLC were used to purify and identify the products of the reaction. 4)
Results and Discussion Synthesis of Compound 3. Scheme 1: Synthesis of Compound 3. To synthesize compound 3, an approach involving treating triptolide with dimethyl sulfide and benzoyl peroxide in acetonitirile was used (Scheme 1). This approach resulted in the formation of compound 4 with a 51% yield and in triptonide (5) with a 46% yield.
The purpose of this lab is to generate an organometallic reagent in solution by reducing a ketone starting material to a tertiary alcohol using phenylmagnesium bromide. This will be accomplished by utilizing a Grignard reagent. Grignard reagents are highly polarized compounds that result in being a strong nucleophile and a strongly basic reagent. Because of this, they are highly sensitive to protic solvents. In order to not have the Grignard react with the protic solvetns, diethyl either will be used as an aprotic solvent. The product of this expirment will not be a reacmic mixture because of the symmetrical nature of the alcohol product, triphenylmethanol.
The purpose of this experiment was to demonstrate necessary steps of the transformation of camphene to isobornyl acetate. After the isobornyl acetate was formed, it was separated from the reactants. Above is a reaction scheme that shows the reaction that occurs when sulfuric acid and acetic acid are added to camphene. The addition sulfuric acid promotes a rearrangement of camphene, and then acetic acid was added. The acetate from this was added to the rearranged camphene, resulting in a formation of isobornyl
Nucleophilic Addition of Bromine Discussion: The goal of this lab is to create 1-bromobutane through the nucleophilic addition of bromine to 1-butanol. Sulfuric acid is used on this lab to help protonate the alcohol, thereby transforming it into water thus making a better leaving group. The bromide ion can then attack and allow for the formation of 1-bromobutane. The reaction starts through a reflux.
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.
The presence of tertiary alcohols creates an increase in the competitive elimination reaction when treated with phosphorus trihalides. To produce a decent yield of tertiary alkyl halides the tertiary alcohols should be treated with concentrated hydrogen halides (1). Creating 2-chloro-2-methylbutane from 2-methyl-2-butanol and hydrochloric acid is an SN1 reaction that demonstrates the transformation. This mechanism can be shown
The purpose of this lab was to synthesize triphenylmethanol from benzophenone and bromobenzene by the formation of a Grignard compound with the reagents bromobenzene and magnesium metal. The bromobenzene was first transformed into the Grignard compound and was then reacted with the benzophenone to make the final product. The mixture was then mixed with sulfuric acid and the organic layer was extracted via a separatory funnel. The mixture was then recrystallized from methanol and was allowed to dry and the percent yield, melting point, and the IR was obtained. The mass of the product obtained was 5.45 grams and the percentage yield was determined to be 41.95%. The melting point range obtained from the final product was 89-91°C
Conversion of Alcohols to Alkyl Halides Lead Author: Mallori Mays Reviewer: Mallori Mays Editor: Mallori Mays Introduction: In this experiment an alcohol was converted to an alkyl halide by both an SN1 and SN2 reactions. Products were obtained by reflux and simple distillation and collected for running spectroscopy data. There are several different Spectroscopy methods used to observe the effects from when light interacts with molecules, depending on the wavelength of light that is used.1 From experiments performed in the past, it is known that UV-VIS uses visible and ultraviolet rays to show any pi bond system with conjugation in the compound, but it is not used for this experiment. IR uses infrared
The first purpose of the lab was to prepare an unknown organomagnesium bromide, an organometallic reagent, reacting an unknown aryl bromide with magnesium in anhydrous ether. The unknown was chosen from a predetermined list of benzoic acid derivatives with varying molecular weights and melting points (see Supplement C). The second purpose of this lab was to prepare an unknown carboxylic acid by reacting the unknown aryl-magnesium bromide with carbon dioxide and diethyl ether then protonating.The third purpose of this lab was to determine the neutralization equivalence point of the unknown carboxylic acid by titrating with sodium hydroxide. The fourth purpose of this lab was to ascertain the identity of the unknown carboxylic acid, and thus the original unknown aryl bromide, using its molecular weight determined from neutralization and melting point.
In this experiment, the purpose was to create and observe the effects of a S_N 1 reaction. Silver nitrate was dissolved in ethanol. The nitrate ion is a decent nucleophile, and ethanol is a fairly powerful solvent. The difference in a SN1 reaction than an SN2 reaction is that a carbocation is formed. The leaving group wants to leave on it’s own, causing a multi-step synthesis.