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organicchemlabfinal - Courtesy of Paul Gonzales No Thanks...

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Courtesy of: Paul Gonzales No Thanks To: Dr. Hee Moon Park Organic Chemistry Final Review 1. The more soluble a component is in the mobile phase (eluent/solvent), the faster it will be transported along the stationary phase (alumina/silica), this allows components to be separated by thin layer chromatography based upon their solubility properties and their attraction to the stationary phases. 2. a) A short fizzing with the production of a foamy white substance occurred after the addition of 6 M HCl to the solution of sodium salicylate. This was the Aspirin separating. b) The change was the reprotonation of sodium salicylate to form Aspirin, which is insoluble in water, therefore, they separated and Aspirin precipitated out of solution. 3. a) 2.20 g * (100 mL / 5.0 g) = 44 mL b) 44 mL * (0.54 g / 100 mL) = .2376 g * Not asked, but if he does* c) Max solid you can recover? 2.2 - .2376 = 1.9624 g 4. After the solution has been through a simple distillation, you will need to prepare a capillary tube to determine the melting point and then use the density of the unknown to confirm your result based upon the melting point. 5. *** MY ANSWERS TO THIS MAY NOT BE CORRECT, BUT WERE CORRECT ON POSTLAB for EXP 6**** a) The HETP value and the number of distillations would be higher. The efficiency would not be changed since the distillation would continue regardless of when you take samples out. The last sample should contain the majority of the toluene, anyways. b) The samples may not be accurate because it would be harder to determine when each sample should be removed from the apparatus, since the bp ranges would be squished together. The efficiency of the experiment would lessen since we would not obtain much of the end result – a pure toluene substance. 6. a) Bromination of Toluene *Bromination of ethylbenzene *Bromination of isopropylbenzene *Bromination of tert-butylbenzene 7. 2-bromo-2-methylpropane + AgNO3 + ethanol ethyl- tert-butyl ether + isobutylene + AgBr (s) 8. a) Eugenol is a phenol because it has a hydroxyl group attached to a phenyl ring. The position of this hydroxyl group is significant in that it allows eugenol to be fairly acidic in comparison to acetyleugenol. This is exploited by treating the crude mixture with a weak base (5% NaOH) that's not strong enough to react with acetyleugenol but it is strong enough to react with eugenol. Hence, NaOH reacts with eugenol, creating anionic compound that is very water-soluble and
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Courtesy of: Paul Gonzales No Thanks To: Dr. Hee Moon Park acetyleugenol is not deprotonated because it is not acidic enough (no phenolichydroxyl group). This allows eugenol to move to the aqueous layer and acetyleugenol to remain in the organic layer and thus be separated by a steam distillation method. 9. Used interchangeably, however, a pure crystalline substance will usually change phase from solid to liquid completely over the range of a few degrees, so melting point is usually used to define where the substance begins to change and range is used to define the complete change.
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