The goal of this experiment was to convert 2-methylcyclohexanol into 1-methyl-1-cyclohexene, 3-methyl-1-cyclohexene, methylenecyclohexane, and water through the addition of phosphoric acid and sulfuric acid. This was done through distillation where a mixture of 2-methylcyclohexanol, phosphoric acid, and sulfuric acid was distilled for 30 minutes in a reflux apparatus. Sulfuric acid being a strong acid acts as a catalyst in this reaction. Phosphoric acid also acts as a catalyst in this reaction. The distillate was then added to a centrifuge tube along with 1-2 ml of saturated sodium chloride. The bottom layer in the centrifuge tube was then extracted and dried using anhydrous sodium sulfate. This bottom layer was then distilled again in
In this experiment, the following chemicals were used; benzocaine, benzoic acid, ethyl acetate, sodium hydroxide, acetone, sodium benzoate, hydrogen chloride, methylene chloride, and glacial acetic acid.
Alkylated phenols and their derivatives are important materials in both organic synthesis and chemical manufacturing. Mono-alkylphenols and di-alkylphenols are used as raw materials for the manufacture of a wide variety of products such as resins, wire enamels, varnishes, printing inks, antioxidants, flame retardants, ultraviolet absorbers, fungicide, petroleum additives and rubber chemicals [1-17]. Friedel–Crafts alkylation of phenol with tert-butyl alcohol (TBA) produces 2-tert-butylphenol (2-TBP), 4-tert-butylphenol (4-TBP), 2,4-di-tert-butylphenol (2,4-DTBP), 2,6-di-tert-butylphenol (2,6-DTBP) and tert-butylphenol ether (TBPE), depending on both the catalyst and the reaction conditions. Based on previous researches, it is well known that moderate acid catalysts or high reaction temperature led to carbon alkylated products and TBPE is produced in the presence of weak acidic catalysts as a major product. 2-TBP is the jarless product of alkylation of phenol with TBA owing to the presence of phenolic (–OH) group on the aromatic ring that kinetically favours o-alkylation. However, due to steric hindrance, thermodynamically unfavoured o-isomer (2-TBP) is readily isomerized into less hindered p-isomer (4-TBP), especially in moderate acidic media. If strong acid catalysts are used in the alkylation reaction, 2,4-DTBP is a dominant product [17,18]. 2,4-DTBP is used in the manufacture of its triphosphite and benzotriazole, which are employed as a co-stabilizer for PVC or UV absorbers in polyolefins [12,13]. 2-TBP is an intermediate for pesticides, fragrances and antioxidants . High selectivity toward 4-TBP is favored since this product imparts enhanced properties to the class of metallic detergents (phenates) used in lubricating oil...
In the lab we produced cyclohexene by dehydrating cyclohexanol using H2SO4. This is an acid catalyzed E1 elimination reaction. The reaction is stabilized by polar protic solvents since it as an E1. A polar protic solvent speeds up the reaction which in turn makes more of the product. Since it was an E1, that means it was a unimolecular elimination. The overall reaction looks like this:
In a separate beaker, acetone (0.587 mL, 8 mmol) and benzaldehyde (1.63 mL, 16 mmol) were charged with a stir bar and stirred on a magnetic stirrer. The beaker mixture was slowly added to the Erlenmeyer flask and stirred at room temperature for 30 minutes. Every 10 minutes, a small amount of the reaction mixture was spotted on a TLC plate, with an eluent mixture of ethyl acetate (2 mL) and hexanes (8 mL), to monitor the decrease in benzaldehyde via a UV light. When the reaction was complete, it was chilled in an ice bath until the product precipitated, which was then vacuum filtrated. The filter cake was washed with ice-cold 95% ethanol (2 x 10 mL) and 4% acetic acid in 95% ethanol (10 mL). The solid was fluffed and vacuum filtrated for about 15 minutes. The 0.688 g (2.9 mmol, 36.8%, 111.3-112.8 °C) product was analyzed via FTIR and 1H NMR spectroscopies, and the melting point was obtained via
An effective oxidation of the secondary alcohol with chromic acid to produce the corresponding ketone. In this report the synthesis of 4-methyl-2-pentanone from 4-methyl-2-pentanol via an adapted jones oxidation1, using diethyl ether as the solvent and concentrated sulphuric acid, is described. An overall yield of 35.74 % was achieved and the product was characterised by NMR, IR and boiling point analysis.
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.
It is also possible for the alcohol product to be prepared from another combination of halides and ketones than the ones used for this experiment. For example, using methyl bromide and 2-heptanone. The Grignard reaction for these starting materials is shown
As a result, the laboratory experiment was determined to be successful and the two product samples obtained and completed calculations displayed that overall bromide was a stronger nucleophile as the chloride ion was more electronegative than bromide, which allowed it to hold electrons in closerE. In conclusion, since bromide is less electronegative and has more electrons, it was able to share the unpaired electrons more easily than chlorideA. These results were expected, as the alkyl bromide would be the major product of procedure A as it followed the SN2 mechanism which was based on nucleophile strength and the product from procedure B would be a near-equal mixture as it followed the SN1 reaction mechanismC. The methods used during this experiment allowed for a successful completion and determination of the better nucleophile, but other additions and observations would have been interesting and beneficial as well. A possible examination of the two sample products collected using pH tested values or observation of sample spotted chromatography paper under a
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