The goal of experiment four was to use sodium dichromate to oxidize borneol to camphor. To purify the camphor use sublimation, then reduce camphor to isomeric alcohol isoborneol with sodium borohydride. Use the 1H NMR to determine the ratio of borneol to isoborneol in the final product. The experiment was carried out by using sodium dichromate to oxidize a borneol solution that was made with borneol and ethyl acetate. Once the reaction was complete the mixture was transferred into a separatory funnel where the ether and aqueous layers were separated and the aqueous layer was then extracted with two portions of ether. All ether layers were combined and extracted once again with 10% sodium bicarbonate and water. Once the ether layer was …show more content…
On the IR spectrum of camphor, a carbonyl functional group (C=O) appeared at 1737 cm-1 with a very large peak. There was also two C-H stretches on the IR spectrum between 2873-2956 cm-1. The SDBS of the true camphor showed all of these same peaks around the same wavenumber. With this observation the oxidation of borneol to camphor was a success. On The IR spectrum of isoborneol, a carbonyl functional group also appeared around 1735 cm-1 but with a smaller peak of the carbonyl group found in camphor. There was two C-H stretches between 2873-2948 cm-1. The spectrum also showed a relatively large hydroxyl group (OH) between 3367-3448 cm-1. The SBDS of the true isoborneol showed all the same peaks around the same wavenumber besides the carbonyl group. True isoborneol does not contain a carbonyl group. Presence of the carbonyl group in the IR spectrum indicated that the reaction didn’t go to completion but it did somewhat reduce camphor into isoborneol because a hydroxyl group formed. If the reaction didn’t go to completion at all and didn’t successfully reduce camphor to isoborneol then a hydroxyl group would not be present. The impurity to the final product would most likely be borneol, because when sublimed for purity the temperature was not controlled and both isoborneol and borneol sublime for
This shows that some impurities are present in the final product. Similarly, the experimental percent yield of 120.2% shows that some issues arose during the procedure. It is impossible to produce a pure product with over 100% yield; therefore, other impurities were present in the product that added weight to the finial mass. This extra weight pushed the yield well over 100%. This source of error could be due to a lack of drying the final product.
Introduction: In this experiment, the identity and absolute configuration of an unknown chiral secondary alcohol will be determined using NMR and CEC. By using the given NMR data, the identity of the alcohol an be determined. In order to identify the stereochemistry of the alcohol, it will have to undergo an esterification reaction in which propionic anhydride, two enantiomers of HBTM(each used in different reactions), and triethylamine are used. Thin layer chromatography will be run at a specified time in the reaction, and the results will be examined both quantitatively(via ImageJ) and qualitatively to which reaction reacted more quickly.
The percent recovery for the acid was 42%, but there was actually 40% of o-toluic acid in the mixture. The extra 2% could be the impurity, 1- 4-dibromobenzene, which would be isolated in the next experiment. The procedure for removing the acid was performed successfully, though. Data Tables 1 also shows the final results in the isolation of the acid.
Chem 51LB Report Ngoc Tran - Student ID # 72048507 The purpose of this lab is to examine the composition of three components of gas products of elimination reaction under acidic condition by conducting the dehydration of primary and secondary alcohol, and under basic condition by conducting the base-induced dehydrobromination of 1-bromobutane and 2-bromobutane. Then gas chromatography is used to analyze the composition of the product mixtures. Gas chromatography (mobile phase) is used to analyze the composition of three components of the gas products. A syringe needle with gas product is injected into the machine, and the component is eluted and the composition is related to the column or the peaks.
The objective of this experiment was to create synthesize methyl eugenol from eugenol, dimethyl carbonate, and tetrabutylammonium bromide. To start off the experiment, a heating under reflux apparatus was used and the parts included: a water jacketed condenser, ring stand, tubes, flowing water, 25-mL round bottom flask, heating block, and a hot plate. There were two parts to the water condenser, entry and exit ways for water. The bottom opening was connected to the sink through one tube and the top opening was connected with a loose end, which was needed to get rid of the flowing water. To create the solution needed to synthesize methyl eugenol, approximately 0.200 g of eugenol (note: the measured g was converted to mg for later calculations) was measured, alongside approximately 1.2 g of TBAB and was added to the 25-mL round bottom flask.
The other points show some possible errors due to the lack of sharpness and length at the peak near 3000. Conclusion Our results showed some possible errors that might have occurred during the reflux. The lack of OH shows a right step towards the production of the Isopentyl Acetate since during that procedure the alcohol group is converted into a carbonyl group (ester).
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.
Lab Report 5: Acetylsalicylic Acid (Aspirin) Synthesis Name: Divya Mehta Student #: 139006548 Date Conducted: November 19th 2014 Date Submitted: November 26th 2014 Partner’s Name: Kirsten Matthews Lab Section: Wednesday 2:30 L9 IAs Name: Brittany Doerr Procedure: For the procedure, see lab manual (CH110 Lab Manual, Fall 2014) pages 96-98. Wilfrid Laurier University Chemistry Department. Fall 2014. Acetylsalicylic Acid (Aspirin) Synthesis.
It is important to allow the ketone to dissolve completely in the solvent in
Also indicative of the ester functional group are the wavelength peaks between 1250-1050cm-1, signaling the presence of -C-O- bonding. Additional peaks in the spectrum, such as the shaky broad peak
The possible explanations and changes to make are similar to the previous questions. Conclusion and Future Experiment 18. The identity of the product and unknown were 4-tert-butylbenzyl phenol ether and tert-butyl phenol respectively. The key to making this discovery was the melting point and TLC results!
This was proved by utilizing the IR spectrum to verify the C =O was not in the final product as it lacked the 1640 cm-1 peak. The melting point of 113-115 degrees C proved that the final product obtained was the E-Stilbene. The TLC plate proved that the E and the Z product was produced, show cased by the double intensity of the DCM spot to the final product’s spot, both which had an Rf of 0.92. The double intensity proved that both products were produced, but through heating and filtering, the Z-Stilbene was
The solution was added to the column. The column sides were rinsed with the solvent to make sure all the solution was on top of the silica gel. The mixture was drained to the top of the silica gel and the solvent was added to fill the column again. The solution of acetylferrocene and the solvent ran through the silica gel. It separated into two bands.
CHAPTER 3 EXPERIMENTAL PROCEDURE 3.1 Materials & Reagents Adsorption of Cu (II) was studied using Montmorillonite-K 10, procured from Sigma Aldrich. It is a very soft phyllosilicate group of minerals that typically form in microscopic crystals, forming clay. Its Cation Exchange Capacity, CEC was 119 meq/100 g .The elemental composition of this clay was [Al1.47Fe0.29Mg0.23][Al0.076Si3.29]O10(OH)2 as reported by the supplier.
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.