Borneol; An Oxidation-Reduction Scheme Nicolas Gibson Lab Time: Tuesday 11:30 am Abstract: 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 …show more content…
There are four main regions of IR absorptions: region 4000 – 3000 cm-1 corresponds to N-H, C-H and O-H stretching, region 2250- 2100 cm-1 is triple-bond stretching , region 2000- 1500 cm-1 is double bonds and the region below 1500 cm-1 is the fingerprint region where a variety of single bonds are absorbed.3 The chromic acid test is a test for oxidizability and gives a positive result for primary and secondary alcohols as well as aldehydes2. A positive result in the chromic acid test is indicated by a color change and the formation of a precipitate. Tertiary alcohols give negative results for the chromic acid test since there must be a hydrogen present on the alcoholic carbon for oxidation to occur. The 2,4 DNP test, tests for a carbonyl and is therefore a dependable test for aldehydes and ketones. Finally, 13C NMR spectroscopy is a test to determine the structure of a compound. 13C NMR detects the 13C isotope of carbon. Each carbon has a different chemical shift. A carbon’s chemical shift is affected by the electronegativity of nearby atoms. Carbons that are bonded to highly electronegative atoms resonant downfield because the electronegative atom pulls electrons away from the nearby carbons and cause those carbons to resonant downfield1 (John McMurry, 2008). A general trend is that sp3-hybridized carbons absorb from 0 to 90 ppm, sp2-hybridized carbons resonant between 110
Lab 8 Purpose Using sodium borohydride as the reducing agent, to convert a ketone (camphor) to a mixture of secondary alcohols (isoborneol or borneol). The product mixture will be characterized by melting point and functional group tests (TLC and IR spectrum). Pre Lab 1. Structure of Camphor NaBH4 used as reducing agent to produce isborneol from camphor Structure of isoborneol Isoborneol with wedged and dashed lines 2. Isoborneol can be produced by reduction of camphor by using the NaBH4 in Methanol.
The oxidation number of an atom of any free element is ZERO. Means to say there is only one kind of atom present, no charge.
The purpose of the PGLO lab was to be able to perform a procedure known as a genetic transformation. We used a procedure to transform bacteria with the gene that codes for a Green Fluorescent Protein (GFP). The actual source of the GFP gene that we used in this complicated experiment is the bioluminescent jellyfish Aequorea victoria. This protein causes the jellyfish to glow under a UV light that was provided in the dark. After the transformation procedure, the bacteria showed their newly acquired gene from a jellyfish and produced the fluorescent protein, which as a result, causes it to glow. If the bacteria glowed in the dark, that was the initial sign that the experiment was successful.
The purpose of this lab was to identify unknown bacteria cultures using various differential tests, and my unknown bacteria is #17. The identification of these unknown cultures was accomplished by separating and differentiating possible bacteria based on specific biochemical characteristics. Whether the tests performed identified specific enzymatic reactions or metabolic pathways, each was used in a way to help recognize those specifics and identify the unknown cultures. The differential tests used to identify the unknown cultures were Gram stain, Catalase, Mannitol Salt Agar (MSA), Blood Agar, Novobiocin, Coagulase, and DNAse (Alachi, 2007).
The mole is a convenient unit for analyzing chemical reactions. Avogadro’s number is equal to the mole. The mass of a mole of any compound or element is the mass in grams that corresponds to the molecular formula, also known as the atomic mass. In this experiment, you will observe the reaction of iron nails with a solution of copper (II) chloride and determine the number of moles involved in the reaction. You will determine the number of moles of copper produced in the reaction of iron and copper (II) chloride, determine the number of moles of iron used up in the reaction of iron and copper (II) chloride, determine the ratio of moles of iron to moles of copper, and determine the number of atoms and formula units involved in
Before the start of the experiment, the theoretical yield was to be calculated. First, the limiting reagent was determined from the reagents by comparing the amount of moles. Among the three reagents involved in this experiment - camphor, sodium borohydride, and methanol, camphor was found to be the limiting reagent. The moles of camphor was less than the combined moles of the other two reagents. The theoretical yield, which is the amount of product that could be possibly produced after the completion of a reaction (“Calculating Theoretical and Percent Yield”), was found to be 0.25 g. Once the product was achieved, a percent yield of 97% was determined. As a result, the reduction of camphor to isoborneol was successful.
The purpose of this experiment was to perform a reduction reaction using camphor in methanol with sodium borohydride. This reaction generated a mixture of diasteroemers; bornoel and isoborneol. NMR analysis was used to determine the product ratio of isoborneol to borneol. In this experiment, 100 mg of camphor, appearing as white crystals, were dissolve in 1 mL methanol. Four portions of approximately 25 mg of sodium borohydride were added.
To prevent the escape of organic vapors, the reaction mixture is cooled with an ice bath before removing the condenser. The next technique used in this experiment was simple distillation. This is a physical separation of the components of the mixture. This technique is accomplished once the drip rate of the product into the collection vessel diminishes considerably. After the reflux and distillation is complete 13C NMR and IR is used to identify the product or products for each reaction. 13C NMR is used to observe the carbon skeleton of an organic molecule. Analysis of this spectrum allows certain stretches to be observed. An IR spectrum has energy measured as frequency recorded on a horizontal axis and intensity of the absorption on the vertical axis. Analysis of the IR allows us to differentiate between certain characteristics and functional groups in organic chemistry.
Some of the aromatic protons were hard to distinguish due to their overlapping nature and resonance. At the same time, there was still enough evidence to verify that the unknown aldehyde was p-anisaldehyde using the number of signals, the chemical shifts, the proton integration, and the splitting patterns. The expected number of signals was roughly 5 peaks, however there were some impurities present in the NMR spectrum. The aromatic region contained the peaks of Hb and Hc with a chemical shift and an integration value of 7.570 and 6.931 ppm respectfully. With that, the protons Hd and He were very distinguishable from the rest of the spectrum due to their large J-value of 16.
Results 0.981 grams of camphor and 1.007 grams of sodium borohydride were used initially. After the recovery, the final mass of the isoborneol was 0.047 grams and melting range was 189.3 - 207.2 C˚. Using the percent yield equation, the percent recovery of isoborneol was found to be 4.73%. From the IR spectrum, the major product was determined to be isoborneol. Discussion During the experiment, the method of recrystallization, isolation and purification were used to isolate the camphor using the sodium borohydride as a reducing agent to form isoborneol and borneol.
Aims: To evaluate the residual antimicrobial effects and surface alterations of gutta percha disinfected with four different solutions.
In two weeks of genetic transformation, we were able to successfully complete the objectives of the lab by correctly performing a transformation of bacterial cells. During the lab, we were able to successfully complete the components that were necessary for a transformation of bacterial cells. Viable cells were transformed, able to grow, and were put in a sterile environment conducive to growth. With the exception of the plate labeled LB/Amp: -pGLO, our results followed the lines of a successful experiment. The LB/Amp: -pGLO plate was contaminated and had colony growth in it. In order for the transformation to be completely successful the LB/Amp: -pGLO plate would have had zero colony growth. As stated in the laboratory manual, biotechnologists
The overall goal in this lab was to oxidize borneol, a secondary alcohol, into camphor, which is a ketone. For the purposes of oxidation chromic acid was utilized, which was prepared by adding a 1:1 ratio of chromium trioxide to dilute sulfuric acid.
Everyday society passes by minute details with no regard what so ever for the magnificent organism that functions to produce an essential gas vital for the human life. This magnificent organism are the various leaves one may find in backyards to parks to school. Although they are small and disregarded, they have various forms that are each unique to certain regions. Therefore the purpose of the lab is to explore the different types of leaves in different environment with different climates. Its significance is that we individual can observe how various factors affect the leaves in a specific area. The experiment will take place at Fullerton’s local university, California State University Fullerton. They possess an incredible arboretum that
The final project of the Spring 2018 Foundations of Biology lab focuses on investigating variation in a population. As a class we study population variation to better understand evolution and the mechanics behind it. What is the basis of evolution? The basis of evolution is the differences in the alleles carried by the members of the population in their genome. The differentiation in allele frequency accounts for a majority of the observable hertable differences in a population. Specifically in this project we are anaylzing variation in the population of our Foundations of Biology class. The main objective of this experiment is to investigate the genetic variation in the Foundations of Biology class by looking at two specific