Camphor Reduction Lab Report

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.

In this lab, the oxidation of a secondary alcohol was performed and analyzed. An environmentally friendly reagent, sodium hypochlorite, was used to oxidize the alcohol, and an IR spectrum was obtained in order to identify the starting compound and final product. The starting compound could have been one of four alcohols, cyclopentanol, cyclohexanol, 3-heptanol, or 2-heptanol. Since these were the only four initial compounds, the ketone obtained at the end of the experiment could only be one of four products, cyclopentanone, cyclohexanone, 3-heptanone, or 2-heptanone. In order to retrieve one of these ketones, first 1.75g of unknown D was obtained.

With this information, the stereochemistry of the alcohol can be deduced. Theory: The competing enantioselective

Diphenyl ether (2 mL) was added to the reaction tube and the reaction tube was heated again until all of the solid dissolved. Then the reaction tube was cooled to room temperature and toluene (2 mL) was added to the tube and placed in an ice bath. Finally the product was collected using vacuum filtration and washed with toluene. The light brown product was dried and weighed (0.088 g, 0.165 mmol,

Title of experiment: Sequence B: The stepwise synthesis of Nylon-6,6 Oxidation of cyclohexanol: Adipic acid Student’s Name: Nico John McQuiston Lab partner’s name: Christine Sullivan Instructor’s & TA’s name: Dr. Behnoush Memari Date Of Experiment: 9/18/2014 Abstract The purpose of this experiment was to prepare nylon-6,6 utilizing step-growth polymerization.

Dehydration of 2-Methylcyclohexanol Sura Abedali Wednesday 2:00 PM January 31, 2018 Introduction: Dehydration reactions are important processes to convert alcohols into alkenes. It is a type of elimination reaction that removes an “-OH” group from one carbon molecule and a hydrogen from a neighboring carbon, thus releasing them as a water molecule (H2O) and forming a pi bond between the two carbons1. In this experiment, 2-methylcyclohexanol undergoes dehydration to form three possible products: methylenecylcohexane, 1-methylcyclohexene, and 3-methylcyclohexene in a Hickman still apparatus. Adding 85% Phosphoric Acid to protonates the “-OH” group, turning it into a better leaving group and initiating the dehydration reaction.

Experiment 7A: Carbonyl Reduction: Sodium Borohydride Reduction of 4-tert-Butylcyclohexanone Experiment 7A, Carbonyl Reduction: Sodium Borohydride Reduction of 4-tert-Butylcyclohexanone, provides firsthand experience with carbonyl reductions. NaBH4, a mild reducing agent, was used to reduce the ketone functional group in the compound, 4-tert-Butylcyclohexanone, that was then protonated using hydrochloric acid to produce two diastereomers (cis/trans) of 4-tertbutylcyclohexanol. Moreover, this experiment refined skills in using H-NMRs (integration, multiplicity, and coupling constants) to effectively distinguish between cis and trans isomers of a desired product. To begin the experiment, 50 mg of 4-t-butylcyclohexanone and methanol were added to a conical vial. NaBH4 was then added to the reaction mixture to reduce the ketone functional group (present in the starting material).

Using filtration sodium acetate was separated, and the filtrate was evaporated to obtain syrup and fractionated at a boiling point of 133-136 °C. The obtained product dissolved in hydrogen bromide of glacial acetic acid and this mixture reaction kept in an ice bath for 1hr. According to procedure, the product was methylated to obtain 1bromo-2, 3, 4, 6-tetramethylglucose.

In this experiment, 9-fluorenone, a ketone, was reduced to fluorenol, an alcohol. The product was then identified using melting point and IR data, and percent yield was calculated. Reduction is one of the two processes that occur during a redox reaction, and it involves the gain of an electron by one of the species. The other species in the reaction loses an electron, and is by definition oxidized. In this experiment, fluorenone, the oxidizing agent, was reduced, and sodium borohydride, the reducing agent, was oxidized.

Week 1 a simple condensation reaction between benzaldeyde and hydroxylamine produced the product benzaldehyde oxime that was found to be in oil. The percentage yield of the experiment is 64%. The 36% loss can be due to the solution needing to be neutralised with glacial acid, there was no way to tell if the reaction was neutralised, to help increase yield the use of pH indictor paper to indicate whether the reaction was neutralised. As by using a rotary evaporator to remove the organic solvent may have caused small amounts of the product to evaporate off as it a low melting point solid, if the water bath temperature was too high would have caused to melt and evaporate off. As melting point was not measured was unable to tell whether the product is pure.

The purpose of this experiment was to identify the two components of an unknown mixture through diverse experimental techniques such as recrystallization, extraction, melting point, and acid-base reactions. From this, the group to which these two compounds belong to had to be determined. These groups are: Carboxylic Acids, phenols, and neutrals. By determining the melting points of the two unknown compounds, these values were compared to the values of melting points in the chart and the proper compound was selected. For the case of this experiment, the unknown mixture contained, 4-methylbenzoic acid.

Rose Bengal-(bis(aminoethyl)ethylene glycol) (2) from Rose Bengal disodium salt (1) The synthesis was done following procedure from [15]. Rose Bengal Na+ salt (915 mg, 0.90 mmol) was dissolved in DMF (2ml) and DIPEA (0.312 ml, 1.80 mmol), HATU (308 mg, 0.81 mmol) were added. After activation for 15 min, the mixture was added to O-Bis-(aminoethyl)ethylene glycol trityl resin (309 mg, 0.31 mmol) preswollen in DMF for 2 hours. The coupling reaction wrapped in aluminum foil was allowed to proceed overnight on a nitrogen bubbler apparatus.

To the solution of methanol (50 ml) and KOH (1.1eq), carbon disulphide (1.1eq) was added slowly at room temperature. To the reaction mass, 2-aminophenol (1.eq) was added with stirring. The reaction mass was refluxed for 6 hr on water bath. Completion of the reaction was monitored by TLC. The reaction mixture was poured to a beaker containing ice cold water and acidified with glacial acetic acid (pH 6).

The purpose of this experiment was to learn about metal hydride reduction reactions. Therefore, the sodium borohydride reduction of the ketone, 9-fluorenone was performed to yield the secondary alcohol, 9-fluorenol. Reduction of an organic molecule usually corresponds to decreasing its oxygen content or increasing its hydrogen content. In order to achieve such a chemical change, sodium borohydride (NaBH4) is used as a reducing agent. There are other metal hydrides used in the reduction of carbonyl groups such as lithium aluminum hydride (LiAlH4).

Reaction: Equation of Reaction C5H6 + C4H2O3→C9H8O3 Physical data Structure Name Cyclopentadiene Maleic Anhydride Formula C5H6 C4H2O3 Molecular Weight 66.10g/mol 98.06g/mol Density 0.80g/mL 1.48g/mL Melting Point -86°C 53°C Boiling Point 42°C 202°C Mass Used 0.160g 0.205g Volume Used 0.20mL 0.139mL Moles Used 0.00242mol 0.00209mol Procedure Observations First, 0.20 g of powdered maleic anhydride was added to a reaction tube.