Preparation of Diphenylisoxazoline by a Dipolar Cycloadditio

Preparation of Diphenylisoxazoline by a Dipolar Cycloadditio Aims The aims of this experiment were: to synthesise a diphenylisoxazoline by a 1,3- dipolar cycloaddition reaction this involved the preparation of an oxime which was oxidised to form a rather unstable nitrile oxide which was trapped in situ with an alkene to yield an isoxazoline.; to fully characterise both, the intermediate oxime and the final isoxazoline, with Infra-Red and Proton NMR spectra. Experimental Preparation of benzaldehyde oxime In a fume cupboard, sodium hydroxide (3.5g) was dissolved in water (30mL) in a 100mL conical flask containing a magnetic stirrer bar. The solution was then allowed to cool down to ambient temperature and benzaldehyde (0.5mL) was added followed by hydroxylamine hydrochloride (0.5g). The stirrer was set to a maximum potency to allow for vigorous stiring for about 5 minutes. The conical flask was stopped at this stage. After 5 minutes, the stopper was removed from the flask and further portions of benzaldehyde (0.5mL) and hydroxylamine hydrochloride (0.5g) were added. This sequence was repeated until all the benzaldehyde (total 5.1mL) and hydroxylamine hydrochloride (total 4.2g) were consumed. The reaction mixture warmed up and the solution became homogeneous indicates complete consumption of benzaldehyde. With the aid of a broad-range pH indicator, the reaction mixture was neutralised with glacial acetic acid (à ¢Ã¢â‚¬ °Ã‹â€ 1.6mL). At this stage a few drops of water were added to help dissolving any sodium acetate precipitate formed. The solution was then allowed to cool and the organic material (top layer) extracted with diethyl ether (2 x 30mL) to a 100mL beaker. A few spatulas of magnesium sulphate were added to the beaker to dry the organic extracts. The mixture was filtered off into a round-bottomed flask and the solvent removed on a rotary evaporator. The yield and the IR spectrum of the oil were recorded. 1,3-dipolar cycloaddition reaction Again in a fume cupboard, styrene (2.9mL) and triethylamine (0.3mL) were dissolved in dichloromethane (15mL) in a 100 mL conical flask. Sodium hypochloride solution (25mL, ca. 10% available chlorine) was added whilst stirring with the aid of a magnetic stirrer bar already in the flask. The flask was placed into an ice bath and the oily oxime (2.5g) was added dropwise with the aid of a Pasteur pipette over a period of 15 minutes. Once addition was completed, the reaction mixture was allowed to stir in the ice bath for a further period of 45 minutes. The whole reaction mixture was transferred to a separating funnel where it was allowed to stand for a few minutes before the lower organic phase was extracted. Afterwards, the remaining aqueous phase was extracted with further dichloromethane (15mL) and both organic extracts combined and dried over magnesium sulphate (a few spatulas as required). The mixture was filtered into a round-bottomed flask, to remove the magnesium sulphate. The flask was placed onto a rotary evaporator to remove any remaining solvent. The weight of the crude product was recorded and the same recrystallised from ethanol. An IR spectrum was run through the pure product and the yield recorded. Results Percentage yield Step 1: Preparation of Benzaldehyde Oxime The first step of this experiment was to synthesise the benzaldehyde oxime. The reaction scheme for this synthesis is as follows: Stoichiometric ratio 1à ¢Ã¢â‚¬ °Ã‚ ¡1 Benzaldehyde used = 5.1mL | density benzaldehyde = 1.0415 gml-1, mass = 5.31g (3 S.F.) Molecular mass = 106.12 gmol-1, therefore n. of moles = (3 S.F.) NH2OHà ¢Ã‹â€ Ã¢â€ž ¢HCl used = 4.2g | Molecular mass = 69.5 gmol.1, hence n. of moles = NaOH used = 3.5g | Molecular mass = 40 gmol.1, hence n. of moles = Experimental ratio Stoichiometric ratio 1à ¢Ã¢â‚¬ °Ã‚ ¡1, hence benzaldehyde is the limiting reagent. N. of moles of benzaldehyde = n. of moles of benzaldehyde oxime Benzaldehyde oxime yield = 4.43g |Molecular mass = 121.139 gmol.1, thus n. of moles = Step 2: 1,3-dipolar cycloaddition reaction The preparation of the diphenylisoxazoline by a 1,3-dipolar cycloaddition follows the following reaction scheme: Benzaldehyde oxime used = 2.50g | Molecular mass = 121.14 gmol-1, therefore n. of moles = Styrene used = 2.90mL = 2.64g | Molecular mass = 104.15 gmol-1, hence n. of moles = NaOCl (ca. 10% available Cl) used = 25 mL | density NaOCl = 1.206 gmL-1, hence 30.15g used. Molecular mass = 74.5 gmol-1, therefore n. of moles = C6H15N used = 0.3 mL | density C6H15N = 0.726 gcm-3, hence 0.218g used. Molecular mass = 101.19 gmol-1, therefore n. of moles = Stoichiometric ratio of benzaldehyde oxime reacting with styrene is of 1à ¢Ã¢â‚¬ °Ã‚ ¡1 Benzaldehyde oxime is the limiting reagent N. of moles of benzaldehyde oxime = n. of moles of diphenylisoxazoline Yield of diphenylisoxazoline = 1.00g | molecular mass = 223.270 gmol-1, thus n. of moles = Overall % yield Spectroscopic data Coupling Constants: H8 at CD: 2J8,7 = 16.4 Hz , 3J8,6 = 8.4 Hz H7 at CD: 2J7,8 = 16.4 Hz , 3J7,6 = 11.2 Hz H6 at CE: 3J6,7 = 11.2 Hz, 3J6,8 = 8.4 Hz Infra-Red Spectra Benzaldehyde Oxime O-H- (stretch) à ¢Ã¢â‚¬ °Ã‹â€ 3500-3100 cm-1, broad peak C=N- à ¢Ã¢â‚¬ °Ã‹â€ 1650 cm-1 sp3 C-H à ¢Ã¢â‚¬ °Ã‹â€  3100-2750 (including aldehyde sp3 C-H) C=C aromatic à ¢Ã¢â‚¬ °Ã‹â€  1450-1500 cm-1 ­ (3 medium peaks). N-OH à ¢Ã¢â‚¬ °Ã‹â€ 960 cm-1 3,5-Diphenyl-2-isoxazoline N-O à ¢Ã¢â‚¬ °Ã‹â€  920 cm-1 (sharp, medium) sp3 (phenyl) C-H and sp2 (azoline) C-H (stretch) à ¢Ã¢â‚¬ °Ã‹â€ 2800-3200 cm-1 C-O à ¢Ã¢â‚¬ °Ã‹â€ 900 cm-1 (sharp, strong) C=C aromatic à ¢Ã¢â‚¬ °Ã‹â€  1450-1500 cm-1 ­ C=N- à ¢Ã¢â‚¬ °Ã‹â€ 1650 cm-1 (sharp, weak) Other Data Before the organic phase was extracted, during the synthesis of benzaldehyde oxime, the reaction mixture was neutralized with glacial acetic acid, as per stated in the experimental session of this paper. The amount of acid necessary was calculated as follows, in order to ensure an accurate amount of acid added to the reaction mixture: N. of moles NaOH = NH2OHà ¢Ã‹â€ Ã¢â€ž ¢HCl n. of moles = Excess of NaOH used = à ¢Ã¢â‚¬ °Ã‚ ¡ n. of moles of CH3CO2H needed. Molecular mass CH3CO2H = 60.1 gmol-1 , hence mass of CH3CO2H = 1.63g. Density of CH3CO2H = 1.049 g/mL, therefore volume needed à ¢Ã¢â‚¬ °Ã‹â€  1.60 mL Discussion Preparation of benzaldehyde oxime The first step of this experiment: Preparation of benzaldehyde oxime, is a simple condensation reaction between an aldehyde (benzaldehyde) and hydroxylamine. The benzaldehyde oxime prepared was clear oil with a relatively good % yield (73%). The comparison between the infrared spectra of the benzaldehyde oxime in the literature and the one recorded for this experiment (attached in the end of this paper) clearly indicates the successful preparation of the same. The Nujol © peaks are shown more strongly in the prepared spectra, but nevertheless it proves a clear way of identifying the functional groups of this compound. M.p. ranges were not measured, and therefore even though the IR spectrum correlates to the actual oximes, its purity should be treated as questionable. 1,3-dipolar Cycloaddition Reaction In this second step of the experiment, the syn-benzaldehyde oxime produced undergoes hypochlorite oxidation to form the 1,3-dipolar benzonitrile oxide which then reacts with the dipolariphile styrene in a 1,3-dipolar cycloaddition reaction. The benzonitrile oxide is termed 1,3-dipole because of one of the resonance forms in which the formal position of the positive and negative charges are 1,3 with respect to one another. However, the term 1,3 does not directly relate to the position of the charges themselves but to the position of the bonding atoms in the dipolar molecule. In this cycloaddition reaction, the dipole atoms in position 1 and 3 of the benzonitrile oxime (LUMO) bind to the styrene (HOMO) to form diphenylisoxazoline. Benzonitrile oxime contributes four à Ã¢â€š ¬ electrons to the system: two à Ã¢â€š ¬ electrons from the à Ã¢â€š ¬ bond and two non-bonding electrons from the oxygen or nitrogen. On the other hand, the dipolariphile styrene contributes further two à Ã¢â€š ¬ electrons. In total [4 + 2]: an electronically allowed cycloadattion in which all 4 +2 electrons are in the ground state (termal). Depending of the spacial orientation of the styrene in solution, there are two theoretical products possible: 3,4 regioisomer 3,5 regioisomer The reaction therefore allows 5-membered rings synthesis, proceeding with high stereospecificity. The study of spectra data such as infrared and 1H-NMR allows not only the confirmation of the final product but also helps to determine the regioselectivity of the reaction. Infra-red Spectra By evaluation of the spectrum of diphenylisoxazoline, one can confirm the product synthesised. The peaks mentioned in the results session of this paper are indeed in accordance to the 3,5-diphenyl-2-isoxazoline structure. By comparison to the previous oxime spectrum, it is obvious the absence of the OH- group and the formation of a C-O bond. The sp2 hybrydised C-H stretches are also seen in the diphenylisoxazoline spectrum. Diastereostopic Systems and 1H-NMR Spectra Diastereostopic groups are not equivalent and have different chemical shits in NMR. A pair of hydrogens located in a carbon atom adjacent to a stereocenter is expected to be diastereostopic. Diastereostopic protons According to Pavia et al, in some compounds with diastereostopic hydrogens, the chemical shifts of Ha and Hb are different and the peaks split each other into doublet of doublets (2Jab). In this case of 3,5-diphenyl-2-isoxazoline, the adjacent proton Hc shows large differences between the vicinal couplings between ac (3Jac) and bc (3Jbc). Refering to NMR results in the results section, the geminal coupling constant between hydrogen 8 and 7 is large. Therefore, the presence of the diastereostopic hydrogens is confirmed as the geminal coupling depends upon the bond angle between both protons. In practice the smaller the angle the larger the coupling constant. H8 at CD: 2J8,7 = 16.4 Hz and H7 at CD: 2J7,8 = 16.4 Hz However, the question remains: Which is the final product: 3,5-diphenyl-2-isoxazoline or 3,4-diphenyl-2-isoxazoline? By using an H-NMR predictor, one can estimate the difference in chemical shifts between the diastereostopic and adjacent protons in both compounds. 3,5-diphenyl-2-isoxazoline or 3,4-diphenyl-2-isoxazoline? The use of an H-NMR predictor will help to understand the final product and its regioselectivity. Spectrum Prediction of H-NMR spectrum of 3,5-diphenylisoxazoline. See references Spectrum Prediction of H-NMR spectrum of 3,4-diphenylisoxazoline. See references As one can see, the chemical shifts predicted for the 3,5-diphenyl product in respect to diastereostopic hydrogens and the methine hydrogens are: à ¢Ã¢â‚¬ °Ã‹â€ 3ppm and à ¢Ã¢â‚¬ °Ã‹â€ 6ppm respectively. On the other hand, the chemical shifts for the 3,4-diphenyl product in respect to diastereostopic hydrogens and the methine hydrogens are: à ¢Ã¢â‚¬ °Ã‹â€ 5ppm and à ¢Ã¢â‚¬ °Ã‹â€ 4.5ppm respectively. The above values for the 3,5-diphenyl product are in close relation to the ones in the results section and hence the final product is the 3,5-diphenyl-2-isoxazoline. For the 3,5-diphenyl-2-isoxazoline, the vicinal coupling are in accordance to the structure of the this regio-isomer. H8 at CD: 3J8,6 = 8.4 Hz H7 at CD: 3J7,6 = 11.2 Hz H6 at CE: 3J6,7 = 11.2 Hz, 3J6,8 = 8.4 Hz The vicinal coupling constant depends upon the dihedral angle between the nuclei. As such, the 3,4-diphenyl product would have very different values. Furthermore, by looking at the structure of both compounds one could say that the 3,4-diphenyl product allows more steric hindrance than the 3,5-diphenyl product. Diazomethane and Ozone Ozone and diazomethane both behave as 1,3-dipoles. Their reactions with styrene also yields 5-membered rings. Ozone with Styrene Resonance forms of ozone as 1,3-dipoles Diazomethane with Styrene Conclusion Both reactions were successful and the products characterized. The regioselectivity of the isoxazoline was analysed by H-NMR spectrum and the product determined to be 3,5-diphenylisoxazoline. Melting point ranges could have helped to determine the purity of the samples. In order to further understand the factors contributing to the regioselectivity product of the 1,3-dipolar cycloaddition reaction, molecular modelling software could be used to determine energy differences between the products and transition states and whether the reaction is thermodynamically or kinetically favoured or both. In conjunction with frontier orbital of both HOME and LUMO and vice versa of the reagents, one could determine the reason for one product being more favoured than other. Nevertheless, the reaction of styrene with 1,3-dipolar benzaldehyde oxime yields 3,5-diphenyl-2-isoxazoline

Lewy Body Dementia

Non-preventable and Non-reversible: Lewy Body Dementia On April 10th 2010, my dad informed me that my grandmother had passed away. She was 90-years-old, and although she may have lived a long life, the last eight or so years of her life were very rough. The official reason she passed away was because of Lewy Body Dementia. This degenerative disease, meaning it is not reversible, is thought to have sprouted from an infection she had in her kidneys in 2002.She lived at home for a while after her kidney disease was found and treated, but was moved to an assisted living center in 2007 because of occasional hallucinations, and family was unable to stay with her at her home. As time progressed, her dementia got worse. She slowly started having hallucinations more frequently, became very forgetful, and eventually was unable to perform any tasks on her own. â€Å"Dementia is a loss of brain function that occurs with certain diseases. It affects memory, thinking, language, judgment, and beha vior,† stated by Google Health. Mayoclinic. om suggests that â€Å"in Lewy body dementia, abnormal round structures — called Lewy bodies — develop in regions of your brain involved in thinking and movement. †Although the specific cause of dementia is unknown, specialists believe that it relates to Alzheimer’s Disease, and Parkinson’s Disease. Evidence of these two diseases has been seen in Lewy Body Dementia (LBD) The cause may not be known, but there are many symptoms that can be easily noticed without difficult tests, such as detailed hallucinations, trembling hands, delusions, sleep difficulties, and more. A clinical diagnosis of LBD can be probable or possible based on different symptom combinations,â€Å" discusses Lbda. org, the Lewy Body Dementia Association website. A probable diagnosis consists of dementia plus two or more core features, or dementia plus a single core feature and one or more suggestive features. A possible diagnosis is dementia plus one core feature, or dementia and one or more suggestive features.Core features are changing cognition with variations of attention or alertness, very detailed hallucinations, and unconsciously having Parkinson’s Disease movements. A suggestive feature includes REM sleep behavior disorder, sensitivity to neuroleptics (a drug used for calming), and low dopamine transporter uptake in the brains basal ganglia, which connects to main parts of the brain like the cerebral cortex and thalamus. LBD cannot be cured, it can only be slowed down. Since there is no cure, doctors can only treat individual symptoms.They use medications for Alzheimer’s Disease to increase the levels of neurotransmitters to help with cognition, Parkinson’s Disease, for muscular issues, but these can increase hallucinations and delusions. Also, doctors may use an antipsychotic medication, which is a neuroleptic, and many LBD patients are severely sensitive to these. Some simple therapy can also be used, such as removing clutter and background noise from the environment, and breaking tasks into simpler steps which will help them focus.Also, how a caregiver responds to a person with LBD is crucial. They should not quiz the person, or question them, they should just validate any concerns, which will usually get rid of the issue at hand for the moment. Lewy Body Dementia is not preventable, but there are certain risks that make it more likely for one to have it when they are older, such as being over 60, being male, and having history of dementia in the family. In conclusion, LBD is an issue that has an effect 15-35% of all dementias, virtualmedicalcentre. com confirms.I have realized that I will probably be diagnosed with this when I am older, because my grandma, and great-grandma on my dads side both had this, and my great-grandma on my moms side is getting the beginning signs of LBD. Because of research, we can understand why certain things happen to us, an d how they happen.Works Cited â€Å"Dementia. † Google Health. Web. 30 Oct. 2010. . Mayo Clinic Staff. â€Å"Lewy Body Dementia – MayoClinic. com. † Mayo Clinic Medical Information and Tools for Healthy Living – MayoClinic. com. 17 Sept. 2010. Web. 30 Oct. 2010. . Welcome to the Lewy Body Dementia Association. Web. 31 Oct. 2010. .

Inclusion Of A Special Education Student - 1243 Words

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Spontaneity Is An Intriguing Personality Trait - 1090 Words

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