The Reduction Of 4 Tert ¬ -butylcyclohaxanone

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.

Purpose: To determine the percent magnesium by mass in magnesium oxide and to observe if the percentage composition is constant by comparing class results.

The dehydration of 2-Methylcyclohexanol was completed using an acid-catalyzed dehydration reaction between 2-Methylcyclohexanol and sulfuric acid. In this acid-catalyzed dehydration reaction, the oxygen atom is first protonated, the oxonium ion is then endothermically decomposed into a carbocation and water, and finally the loss of a proton from an adjacent carbon atom forms an alkene. Due to the presence of carbocation rearrangement, three products are formed as shown below in Figure 1.

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

A 0.5 g of sodium tungstate dihydrate was weighed and transferred into a 50-mL round-bottom flask with a magnetic stir bar. Approximately 0.6mL of Aliquat 336 was then transferred carefully into the round bottom flask using a 1mL syringe. The round bottom flask and its contents were then set up in an oil bath. 11mL of 30% hydrogen peroxide and 0.37 g of potassium bisulphate were added to the reaction mixture in the round bottom flask and stirred using a magnetic stirrer. Lastly, 2.5mL of cyclohexene was added using automatic dispenser and the mixture stirred. A condenser was fitted on the round bottom flask, clamped and attached to water horses. The reaction mixture was then heated on the oil bath and the reflux process initiated for an hour while stirring the mixture vigorously. Half way while rinsing, any trapped cyclohexene in the condenser was rinsed. After 1 hour, the round bottom flask was rinsed

The Purpose of this experiment is for the students to learn how to use sodium borohydride to reduce benzil to its secondary alcohol product via reduction reaction. This two-step reaction reduces aldehydes by hydrides to primary alcohols, and ketones to secondary alcohols. In order for the reaction to occur and to better control the stereochemistry and yield of the product, the metal hydride nucleophile of the reducing agents such as LiH, LiAlH4, or NaBH4 must be carefully chosen. Being that LiAlH4 and NaBH4 will not react with isolated carbon-carbon double bonds nor the double bonds from aromatic rings; the chosen compound can be reduce selectively when the nucleophile only react with

14 mL of 9 M H2SO4 was added to the separatory funnel and the mixture was shaken. The layers were given a small amount of time to separate. The remaining n-butyl alcohol was extracted by the H2SO4 solution therefore, there was only one organic top layer. The lower aqueous layer was drained and discarded. 14 mL of H2O was added to the separatory funnel. A stopper was placed on the separatory funnel and it was shaken while being vented occasionally. The layers separated and the lower layer which contained the n-butyl bromide was drained into a smaller beaker. The aqueous layer was then discarded after ensuring that the correct layer had been saved by completing the "water drop test" (adding a drop of water to the drained liquid and if the water dissolves, it confirms that it is an aqueous layer). The alkyl halide was then returned to the separatory funnel. 14 mL of saturated aqeous sodium bicarbonate was added a little at a time while the separatory funnel was being swirled. A stopper was placed on the funnel and it was shaken for 1 minute while being vented frequently to relieve any pressure that was being produced. The lower alkyl halide layer was drained into a dry Erlenmeyer flask and 1.0 g of anhydrous calcium chloride was added to dry the solution. A stopper was placed on the Erlenmeyer flask and the contents were swirled until the liquid was clear. For the distillation

After the crude product was collected by crystallization process, it was weighted to be 8.4756 g. it was recrystallized and collected. The weight of pure product was obtained to be 5.772 g In comparison to the theoretical yield of the experiment; it was calculated to be 65.99 % recover and 82% total yield. The melting point (MP) of the product was taken in order to identify the product. 2 trials were performed, and the results of both trials are the same, 102-105oC. The expected product of this experiment was dibenzalacetone, which has 3 different isomers: cis-cis, trans-trans, and cis-trans, with different MPs and boiling point (BP). The true MP of Trans-trans dibenzalacetone isomer is 110-110oC (ref. 3). The true MP of cis-cis dibenzalacetone isomer is 60oC (ref. 3). Cis-cis dibenzalacetone doesn’t have MP because its appearance is oil (ref.3). In, comparison to all the isomers, the product’s MP was closet to trans-trans dibenzalacetone, although the product MP was lower than the true MP of trans-trans dibenzalacetone. There were some possible reasons why the MP of the product was lower. The intermediate, benzalacetone with the MP of 42oC (Ref. 2), could be existed in the product resulting in lower the MP of the product. Another reason could be that the cis-trans isomer of dibenzalacetone existed in the product. In order to confirm which reason is the case, infrared spectrum (IR) (see attached

The sodium hydroxide acts to pull the hydrogen off the oxygen in the 2-methylphenol so that the oxygen has a negative charge and can attack the sodium chloroacetate. Again, using a 1:1 molar ratio, 0.34 g (2.9 mmol) of sodium chloroacetate (the good leaving group) was added to 1 ml of water and dissolved. Following dissolving all of the 2-methylphenol (to avoid the sodium hydroxide reacting concurrently with the sodium chloroacetate and 2-methylphenol) in the sodium hydroxide, the aqueous solution of sodium chloroacetate was transferred to the reaction flask. This mixture was then heated to reflux, using a medicine dropper affixed to the top of the flask as an alternative method to boil without

The purpose of this lab was to carry out a dehydration reaction of 2-methylcyclohexanol by heating it in the presence of phosphoric acid and determining which alkene product would be the major product. Methylcyclohexanols were dehydrated in an 85% phosphoric acid mixture to yield the minor and major alkene product by elimination reaction, specifically E1. The alkenes were distilled to separate the major and minor products and gas chromatography was used to analyze the results and accuracy of the experiment. The hypothesis was the major product of the reaction would be the most substituted product. This conclusion was made because of

We began this experiment by weighing out the known values of mass for 1-chloro-2,4-dinitrobenzene and m-aminobenzoic acid which was 1.012g and 0.686g respectively. These values were calculated before the experiement based on the mole ratios of the balanced equation in question. Here the reaction was a 1:1 ratio so we were able to determine the theoretical mass of our product, m-(2,4-dinitroanilino)

In this experiment, the main objective was to synthesize a ketone from borneol via an oxidation reaction and secondly, to produce a secondary alcohol from camphor via a reduction reaction. Therefore, the hypothesis of this lab is that camphor will be produced in the oxidation reaction and isoborneol will be the product of the reduction reaction because of steric hindrance. For the oxidation step, a reflux will be done and then a microscale reflux for the reduction step. The products will be confirmed using Infrared spectroscopy, the chromic acid test, 2,4-DNP test and 13C NMR spectroscopy. The results of this

The reaction took place in a conical vial and .2mL of each of the reactant samples were added to it along with some 95% ethanol. Two drops of NaOH were added shortly after and stirred at room temperature for fifteen minutes. The vial was cooled in and ice bath and crystallized. Vacuum filtration was performed to filter the crude product. The crude product was recrystallized using methanol and filtered again. We made one change to the procedure and instead of using .7mL of ethanol we

5.3 mL of bromobenzne and 15 mL of anhydrous ether was then placed into the separatory funnel and was shaken and vented in order to mix the solution. Half of the bromobenzene solution was added first into the round bottom flask and as soon as a color change was observed, the remaining half of the bromobenzene was added drop wise into the round bottom flask. The mixture was then refluxed on a heating mantle for 10 minutes until most of the magnesium has been consumed.

First, a balance was used to measure 0.55 grams (g) of white, crystal benzophenone and 0.06 g of white, powder sodium borohydride. The two solids were placed into a 25 milliliter (mL) round bottom flask. A couple of boiling chips and 3 mL of 2-propanol were then poured into the flask. The 2-propanol measured with a graduated cylinder was a clear liquid, but once added to the flask with benzophenone and sodium borohydride became a cloudy white solution. A reflux was performed with a condenser set up vertically and the flask held secure with a metal clamp. The flask was heated with a heating mantle and a Variac® set at 50% of 120 volts (V) to control the temperature. This prevented the vapors from rising above the bottom third portion of the condenser and escaping. The solution started to boil after 4 to 5 minutes and was allowed to boil a consistent rate for 30 minutes. The condensed vapors that dripped back into the flask were clear. The flask was kept in place and the heating mantle was removed. The solution was allowed to return to room temperature with the condenser still attached.