Initially, the conversion of benzyl alcohol in to benzaldehyde was chosen as a model reaction to optimize the reaction conditions. Effect of reaction time and mmol of H2O2 on progress of oxidation reaction was studied (Fig. 4. the experiment was performed with 20 mg catalyst, 10 ml acetonitrile and two different amount of H2O2 1 and 2 mmol for 1mmol benzyl alcohol at reflux condition (85 ºC ) and plotted with respect to the time. With increasing the mole ratio of BzOH : H2O2 from 1:1 to 1:2, the conversion of benzyl alcohol increased from 75% to 93%. The conversion also increased with increasing time of reaction and then remain constant at 180 min. From Fig. 4, it can be deduced that the maximum yield of benzaldehyde was obtained within 2 h when the mole ratio of BzOH: H2O2 was 1:2. …show more content…
It seems that solvents play a pivotal role in the liquid phase catalytic reaction. The conversion of benzyl alcohol is 5% under solvent-free conditions (Table 1, entry 1). The conversion percentage of benzyl alcohol are different in nonpolar to polar solvents. As demonstrated by Table 1, the conversion of benzyl alcohol is 40%, 62%, 93% and 10% when n-hexane, toluene, acetonitrile and H2O are used as solvent, respectively (Table 1, entries 2-5). This indicates that aprotic acetonitrile with large dielectric constant promote the collisions and dispersion of oxygen source, the alcohol and the catalyst [15]. Furthermore, acetonitrile can form a perhydroxyl anion (OOH-) and activate the hydrogen peroxide. Perhydroxyl anion can attacks the nitrile to produce a peroxy carboximidic acid intermediate, which can act as an oxygen transfer agent and improve the conversion
Abstract: In this experiment, triphenylmethanol was synthesized in two steps. First, the bromobenzene was reacted with dry magnesium turnings to produce Grignard reagent. Second, the Grignard reagent was reacted with methyl benzoate and concentrated sulfuric acid to produce an alcohol. The end result of the experiment was not very successful because only 17% yield of final product triphenylmethanol was recovered, and the final product was impure based on the melting point and the IR spectrum results.
Grignard is a reaction that is crucial to forming the new carbon-carbon bond. This is a two-part lab that teaches new techniques; the purpose of this lab is to introduce realistic organic synthesis and apply acid workup to produce triphenylmethanol. A Grignard reaction is characterized by the addition of a magnesium halide (an organomagnesium halide) to an aldehyde or a ketone in order to form a secondary or tertiary alcohol. These reactions are helpful because they serve as a crucial tool in performing important carbon-carbon bond-forming reactions (Arizona State University, 2018). This experiment aimed to observe the mechanisms of a Grignard reply to synthesize triphenylmethanol from benzophenone using phenylmagnesium bromide as the Grignard reagent.
The goal of the experiment is to synthesize a bromohexane compound from 1-hexene and HBr(aq) under reflux conditions and use the silver nitrate and sodium iodide tests to determine if the product is a primary or secondary hydrocarbon. The heterogeneous reaction mixture contains 1-hexene, 48% HBr(aq), and tetrabutylammonium bromide and was heated to under reflux conditions. Heating under reflux means that the reaction mixture is heated at its boiling point so that the reaction can proceed at a faster rate. The attached reflux condenser allows volatile substances to return to the reaction flask so that no material is lost. Since alkenes are immiscible with concentrated HBr, tetrabutylammonium bromide is used as a phase-transfer catalyst.
In addition, phenolphthalein was added as an indicator. The aliquots were titrated against sodium hydroxide (NaOH) solution until end point was reached, after which volume of NaOH consumed was recorded. The value of the rate constant, k, obtained was 0.0002 s-1. The experiment was then repeated with 40/60 V/V isopropanol/water mixture and a larger value of k = 0.0007 s-1 was obtained. We concluded that the rate of hydrolysis of (CH3)3CCl is directly proportional to water content in the solvent mixture.
In this diagram we can see that acetaminophen consists of a benzene ring core, with hydroxyl and amide functional groups in proxy. Benzene (C6H6) is a hydrocarbon composed of 6 carbon atoms (92.26% of the molecule) and 6 hydrogen atoms (7.74% of the molecule) with alternating double and single bonds (resonance bonds) and is aromatic because of this. Benzene is a natural part of petroleum, usually <1.0% by weight, but is found in many things used today. Benzenes most common use is to produce ethylbenzene, with over half of the benzene used in the production of ethylbenzene. Benzene is a clear, colourless and highly volatile liquid which is soluble in water at an average room temperature (23.5o).
The purpose of this experiment was to learn about the electrophilic aromatic substitution reactions that take place on benzene, and how the presence of substituents in the ring affect the orientation of the incoming electrophile. Using acetanilide, as the starting material, glacial acetic acid, sulfuric acid, and nitric acid were mixed and stirred to produce p-nitroacetanilide. In a 125 mL Erlenmeyer flask, 3.305 g of acetanilide were allowed to mix with 5.0 mL of glacial acetic acid. This mixture was warmed in a hot plate with constantly stirring at a lukewarm temperature so as to avoid excess heating. If this happens, the mixture boils and it would be necessary to start the experiment all over again.
Benzyne Formation and the Diels-Alder Reaction Preparation of 1,2,3,4 Tetraphenylnaphthalene Aubree Edwards Purpose: 1,2,3,4-tetraphenylnaphthalene is prepared by first producing benzyne via the unstable diazonium salt. Then tetraphenylcyclopentadienone and benzyne undergo a diels-alder reaction to create 1,2,3,4-tetraphenylnaphthalene. Reactions: Procedure: The reaction mixture was created. Tetraphenylcyclopentadienone (0.1197g, 0.3113 mmol) a black solid powder, anthranilic acid ( 0.0482g, 0.3516 mmol) a yellowish sand, and 1,2-dimethoxyethane (1.2 ml) was added to a 5-ml conical vial.
The reaction to synthesize benzocaine was known as a Fisher esterification reaction. The Fisher esterification was reaction between alcohol and carboxylic acid in the presence of acid. The reaction was used to form an ester. In the experiment, sulfuric acid acted as a catalyst and necessary for this reaction to occur. There was a change between the –OH group of carboxylic acid to an –OCH2CH3 group in the reaction.
The yellow solution containing the reactants was slowly poured into the beaker containing the cold water and the acid in order to cause the precipitation of the alcohol, 9-fluorenol and to destroy (hydrolyzed) the unreacted excess sodium borohydride. Subsequently, the white precipitate was vacuum filtered and washed twice with 20.0 ml portions of distilled cold water by pouring the liquid into the Buchner Funnel during filtration. It was necessary to wash the alcohol prior to recrystallization considering that the C-OH bond is easily broken by the formation of a stable and benzylic carbocation that favors the synthesis of difluorenyl ether. Finally, before the purification by recrystallization of the obtained product, the white solid alcohol was allowed to dry over a period of a
Cross Condensation of aldol 2015007632 Dowrie, K Contents Reaction 1 Introduction 1 Experiment Procedure 2 Experimental results 3 Table of calculations 3 Calculations 3 NMR 4 TLC 4 References 5 Reaction Introduction An aldehyde reaction is when aldehydes and keytones, both containing an α-hydrogen in the presence of an alkali group condenses and forms an enone. Acetone has α-hydrogens on each side. The proton can be removed and therefore giving a nucleophile anion. The aldehyde carbonyl is more reactive than the keytone and so it reacts rapidly with the anion.
It is understood the mechanism is acid-catalyzed where protons coordinate with the carbonyl oxygen to make the carbonyl carbon more electropositive for nucleophilic attack (Scheme 1). In the experimental procedure all reactants were added together, this is inefficient as the protons can coordinate with either trans-cinnamic acid or methanol. Coordination with methanol is unnecessary as it reduces its nucleophilicity and makes less protons available to coordinate with the carboxylic acid. To improve
In the synthesized Friedel-Craft acylation reaction mechanism, anisole (methoxybenzene) is the nucleophile. The double bond on the nucleophile attacks the electrophile acetyl. The acetyl compound is then bound to the anisole in the para position, which created the product p-methoxyacetophenone. Since anisole is an activator (electron donor), the acetyl could have bound in either the ortho or para position (or in the meta position, but it is not as likely). However, the reason that acetyl was not bound in the ortho position was because the para position demonstrated the least amount of steric hindrance.
Purpose/Introduction The process of recrystallization is an important method of purifying a solid organic substance using a hot solution as a solvent. This method will allow the separation of impurities. We will analyze Benzoic Acid as it is dissolved and recrystallized in water and in a solvent of Methanol and water. Reaction/Summary
Reaction is carried out in a 500 ml three-neck flask supported on a heating mantle and provided with a mechanical stirrer, a water condenser, a thermometer probe with an inlet for dry nitrogen gas, and an addition funnel. The calculated amount of IPDI and THF are charged to the three- neck flask under mechanical stirring and BTMSPA is added slowly from the addition funnel at a rate to maintain the reaction temperature below 50°c. After addition of BTMSPA is complete, mixture is stirred for additional 1 hour at room temperature. The completion of the reaction is verified by FT-IR following the disappearance of peak associated with NCO groups. The obtained solution is transferred to a single-neck flask and by using a rotary vacuum evaporator THF is distillate in two steps and replaced by dry ethanol to yield around 60-65% solution.
Abstract The unknown concentration of benzoic acid used when titrated with standardized 0.1031M NaOH and the solubility was calculated at two different temperatures (20◦C and 30◦C). With the aid of the Van’t Hoff equation, the enthalpy of solution of benzoic acid at those temperatures was determined as 10.82 KJ. This compares well with the value of 10.27KJ found in the literature.