Synthesis Of Heterocycles Lab Report

3. The IR spectrum of the starting material shows a medium/strong C-O bond at around 1500cm-1, also the starting material shows a strong C-H bond at around 3000cm-1 and another medium C-H bond at 2865cm-1 indicating an aldehyde group whereas the product does not. The IR spectrum of the product shows a two weak broad O-H peaks at around

The benzene molecules replace 3 of the CO bonds and rest parallel to the plane of the remaining CO groups. The products geometry is such that it can be considered octahedral as opposed to tetrahedral. The carbonyl to molybdenum bonds are close to 90 degrees instead of 109.5 which is indicative of a tetrahedral complex. Using H NMR and infrared spectrum it is possible to analyze the product and determine its relative structure and composition. CO stretches have unique places within the spectrum and thus can be noted. H NMR can be used to determining the structure by comparing it to that of mestylene. Looking at these spectrum’s allows for one to look for indication of methyl group

Based on the 1H NMR spectrum that was collected, a few things can be determined. Based on deshielding and electronegativity, the peak that occurs around 4.7ppm is associated with the O-ethylsaccharin product and the peak at 3.8 ppm is associated with the N-ethylsaccharin product. Based on the height ration, the N-ethylsaccharin product is the more prevalent result.

The unknown NMR/IR Unknown #7 was C8H11N. The first in determining the structure from looking at the NMR spectra was to determine the degrees of saturation (DoU). DoU helps identify the number of bonds within the compound. The DoU can be determined by looking at the chemical formula and using the equation, DoU= (2C + 2 + N - X – H)/ (2). For this particular compound, I identified that the DoU was 4. Next, using the given IR peak, as well as looking at the chemical formula, the weak wavelength of 3400 cm-1 was identified as a amine function group, and that particular peak was a N-H bond stretch. Next the NMR spectra was examined. Using the spectra, I noticed there were four different peaks, The first peak was a singlet around 7.3-7.3 ppm and only had one hydrogen on the compound.

Identifying this organic acid was an extensive task that involved several different experiments. Firstly, the melting point had to be determined. Since melting point can be determined to an almost exact degree, finding a close melting point of the specific unknown can accurately point to the identification of the acid. In this case the best melting point

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

Dictionary of organic compounds, 6th edition, Chapman and Hall, London, Volume 3(& Volume 6), 1996 Maria Lindsay and Sean P. Hickey, Organic chemistry lab 2 manual, department of Chemistry University of New Orleans

The first stage of this multistep synthesis resulted in a successful yield of isobornyl acetate, as stated in Table 2 of page 6. A sample of 1.635 g of isobornyl acetate was produced, which corresponds to an 83.5% yield. The infrared (IR) spectrum illustrated in Figure 1 of page 5 shows the presence of sp3-hybridized carbons around 2990 cm-1. According to Table 2, sp3-hybridized carbons should appear as strong bands in the range of 2850.00-2960.00 cm-1, which holds true for the experimental spectrum. The HC–H and dimethyl signals predicted to appear at 1420.00-1470.00 cm-1 are found at around 1410.00 cm-1 of the experimental spectrum.

140–142 ºC, Yield: 2.39 g (87%). IR (KBr, cm-1), : 3400-2900 (H-bonded O–H), 3080 (C–Harom), 2950 (C–Haliph), 1739 (C=Oester), 1646 (C=Oketonic), 1630 (C=Oquinolinone). 1H NMR (300 MHz, DMSO-d6), : 1.30 (t, J = 7.2, 3H, OCH2CH3), 3.53 (s, 3H, NCH3), 4.31 (q, J = 7.8, 2H, OCH2CH3), 7.36 (t, J = 7.2, 1H, 6-CH), 7.58 (d, J = 8.4, 1H, 8-CH), 7.84 (t, J = 7.5, 1H, 7-CH), 8.11 (d, J = 7.8, 1H, 5-CH). 13C NMR (75 MHz, DMSO-d6), : 190.5, 171.8, 163.6, 160.1, 142.0, 136.2, 125.2, 122.8, 115.5, 113.9, 102.6, 61.8, 28.8, 13.6. MS (m/z, Ir %): 276 (M+1) (3.65), 275 (M•+) (17.45), 247 (5.08), 229 (6.16), 219 (6.63), 203 (13.8), 202 (100) (base peak), 175 (22.89), 161 (7.89), 134 (39.39), 118 (6.22), 106 (24.51), 91 (15.18), 77 (23.25).

8-hydroxyquinoline (8-HQ) is a bicyclic compound derived from quinoline (1-azanaphthalene) and consist of two rings system: carbocyclic ring and pyridine ring with hydroxyl group substituted at position-8. 8-HQ is one of the most popular and versatile organic compound is an organic crystalline material. 8-HQ has typical phenolic properties, e.g. it gives violet colour with ferric chloride, couple with diazonium cations, and participate in Reimer-Tiemann and Bucherer reactions; its acetate ester usually undergoes the Fries rearrangement with aluminium chloride to give acetyl derivative [1]. As a result of the proximity of the hydroxyl group to the heterocyclic nitrogen, 8-HQ forms insoluble chelate complexes with a great variety of metal ions, including Cu2+, Bi2+, Mn2+, Mg2+, Fe3+, Al3+, Zn2+and Ni3+ [3]. The hydrogen of the hydroxyl group in 8-HQ is displaced and the metal is linked to both the oxygen and nitrogen.

The purpose of this experiment was to identify one ketone with Thin Layer Chromatography and one using NMR spectrometry. We will do this by making 2, 4 a DNPH derivative and checking the melting points.

2-methyl-2-butanol was used to form 2-chloro-2-methylbutane with a calculated yield of 23.4% (2.28 g, 21.4 mmol). The major peaks for experimental 2-chloro-2-methylbutane was sp3 C-H stretch 2939-2977 cm-1 and C-Cl 798.29 cm-1. The major shifts in H NMR was δ1.55, s, 6H; 1.73, q, 2H; and 1.03, t, 3H. IR and h NMR indicted little to no contamination.

The identification and characterization of the structures of unknown substances are an important part of Organic Chemistry. In this experiment a sample of an unknown aldehyde or ketone was obtained. From this sample two solid derivatives were prepared. Their melting points were obtained and compared to those listed in the Table of Aldehyde & Ketone Derivatives. From this the unknown sample was identified. As additional aid a Benedict’s test and Iodoform test were used. These are functional group tests used for distinguishing between aldehydes, ketones and methyl ketones. A Benedict’s test tests positive for aliphatic aldehydes and negative for aromatic aldehydes and ketones. An Iodoform test tests positive for methyl ketones and acetaldehyde

The products of Suzuki–Miyaura coupling reaction were characterized by nuclear magnetic resonance spectroscopy (NMR, model 500 MHz, Varian NMR Systems). Detailed information regarding the 1H NMR (500 MHz) and 13C NMR (125 MHz) NMR data are provided in the Supplementary Data. The NMR spectra were referenced to TMS as an internal standard and are reported as follows: chemical shift multiplicity (s = singlet, d = doublet, t = triplet, m = multiplet), coupling constant in Hz, and integration.

(a) M. Katcka, Rocz. Chem. 1977, 51, 1455; (b) A. Reliquent, R. Besbes, F. Reliquent, J. C. Meslin, Synthesis., 1991, 7,