Organic Chemistry Laboratory
Organic Chemistry Laboratory CHEM 550
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This 3 page Class Notes was uploaded by Serena Raynor on Thursday October 29, 2015. The Class Notes belongs to CHEM 550 at University of New Hampshire taught by Staff in Fall. Since its upload, it has received 21 views. For similar materials see /class/231709/chem-550-university-of-new-hampshire in Chemistry at University of New Hampshire.
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Date Created: 10/29/15
Chem 550 G R Weisman Classi cation by Solubility Test H20 solubility 3 Two classes A H20 Soluble B H20 Insoluble A H20 Soluble Compounds Two further tests 1 Measure acidity of H20 solution litmus red acidic RCOOH likely pH lt 45 typical phenols too weak H20 Soluble Compound litmus blue basic 1 2 3 amines aryl amine too weak neutral or weak acid or base ROH ArOHRCHO RCOR RCOZR RCN low mol wt amides unchanged 2 Measure solubility in anhydrous diethyl ether EtZO polar probably monofunctional may be ROH RCHO RCOR RCOZR RCN RCOOH RNHZ RCONHZ etc usually 5 5 carbons H20 Soluble Compound EtZO very polar probably polyfunctional may be glycol salt of acid or amine carbohydrate polybasic acid amino acid etc B H20 Insoluble Compounds Several tests Look at solubility in 5 aq NaOH 5 aq NaHCO3 5 aq HCl and cold conc H2S04 acidic RCOOH 6 or C02 more carbons or HO O NOZ etc 5 NaHCO3 weakly acidic phenol or gt oxime possible H20 Insoluble Compoun 5 NaOH basic 1 2 3 aliphatic amines anilines only one Ar 0w If N or S present then neutral compound like RN02 3 or aryl amide di or triarylamine RCN sulfide disulfide etc 5 HCl If no N or S present one more test see below ROH RCHO RCOR ROR some RCOZR alkene alkyne t some aromatics or reac ion 23 II11Cl Insoluble cold COHC poun H no N or S 2 RH cyclic RH ie alkanes Ar simple aromatics RX ArOAr G R Weisman KBr Pellet Preparation Procedure Using the Mini Press Take the KBr minipress out of the oven and allow it to cool Alternatively cool the press by rinsing with cold water followed by acetone and replace the press in the oven long enough to get warm but not hot Using the small agate mortar and pestle take care 7 expensive grind a few mg a very small spatula tip of your sample until it has a glassy appearance Add 50100 mg of dry KBr from oven to your sample and thoroughly mix with a spatula Do not grind the sample Inspect the press to make sure it is clean Insert one bolt ve full turns into the press Transfer the sampleKBr mixture into the press using a plastic spatula There should be enough so that the entire bolt face is covered Tap the press on the table gently to spread the mixture evenly over the bolt face Insert the other bolt fingertight and then tighten the bolts using wrenches or a torque wrench Mounting the press in a vise is helpful Carefully remove the bolts one at a time The pellet should be clear or translucent Place the press in the press holder and run the IR spectrum Rinse the press and bolts thoroughly with water followed by acetone and return them together to the oven Clean up the area before you leave Preparation of Mull Nujol or Halocarbon Oil Grind NS mg a very small spatula tip of your compound to a ne powder using an agate mortar and pestle Add 1 drop of the liquid mulling agent either Nujol a longchain alkane mixture also call mineral oil or halocarbon oil Grind the mixture with the pestle to the consistency of toothpaste or slightly thinner Add additional mulling agent as necessary Using a plastic spatula transfer the mull to a NaCl plate Place a second NaCl plate on top and press gently to spread the mull between the plates it need not cover all of the plate area Place the plates in the holder and run the IR spectrum Clean the mull from the salt plates Generally CHzClz is a good solvent for this purpose Return the clean salt plates to the desiccator A pliable plastic spatula made from an anglecut plastic drinking straw is ideal for this purpose Avoid the use of a standard metal spatula It doesn t work well and the agate mortar can be scratched
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