CHY252_Lab Notebook
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CHY252_Lab Notebook

Course Number: CHY 252, Spring 2006

College/University: University of Maine

Word Count: 1477

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Lab Notebook Index (Labs go MSDS, Write up, Spectra) Kinetic vs. Thermodynamic Control and Molecular Modeling ---------- 1-3 Diels-Alder Reaction------------------------------------------------------------4-6 Williamson Ether Synthesis ---------------------------------------------------7-9 Nitration of Pipereronal--------------------------------------------------------10-12 Bromination of Acetanilide...

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Notebook Lab Index (Labs go MSDS, Write up, Spectra) Kinetic vs. Thermodynamic Control and Molecular Modeling ---------- 1-3 Diels-Alder Reaction------------------------------------------------------------4-6 Williamson Ether Synthesis ---------------------------------------------------7-9 Nitration of Pipereronal--------------------------------------------------------10-12 Bromination of Acetanilide ---------------------------------------------------13-15 Friedel-Crafts Alkylation-------------------------------------------------------16-18 Isolation of Betulin & Rearrangement to Allobetulin----------------------19-21 Etherification Reactions -------------------------------------------------------22-24 N,N-Diethly-m-toluamine (DEET)-------------------------------------------25-27 Classification Tests for Aldehydes and Ketones---------------------------28-39 Aldol Condensation/2D NMR ------------------------------------------------30-32 Knoevenagel Condensation----------------------------------------------------33-35 Diphenylcyclopropenone------------------------------------------------------36-38 Kinetic vs. Thermodynamic Control and Molecular Modeling Pre-Lab notes: Add .44g morpholine to ice cold flask with .79g t-butyl and 3 sieve beads Distill crystals in t-butyl acetoacetate and a black boiling chip, slowly add morpholine into reaction flask Let flask sit until next class and collect clear crystals from flask Notes: Solution turned rusty-orange color over first week time frame Little to no crystals formed from reaction Collected IR from other groups data via Sunil's orders Percent Yield: 880mg-316mg 880mg = 64.09% Diels-Alder Reaction Pre-Lab notes: Add 2 drops of dimethylacetylenedicarboxylate into reaction tube and take weight(25mg) Weigh out 45mg of tetraphenylcyclopentadienone followed by .4ml of 1,2-dichlorobenzene along with a boiling stone heat solution in sand bath for 10 minutes until color change occurs (didn't occur) cool solution and add .6ml of ethanol, crystallization should occur immediately put reaction flask into ice water and add .5ml of ice-cold methanol into tube, and collect crystals Notes: Solution didn't turn color, results still good however Percent Yield: 82mg-30mg 82mg = 63.14% Williamson Ether Synthesis Pre-Lab Notes: measure out 760mg of vanillin and 300mg KOH into RBF add 15ml ethanol and 3ml water along with 2 boiling stones to RBF attach RBF to condenser apparatus and heat add benzyl chloride to reaction through condenser tube heat for an hour remove KOH crystals via vacuum filtration reheat solution and add 2-4ml of water until solution becomes cloudy as solution becomes cloudy cool flask and watch crystals form vacuum filter crystals out of solution and air dry them Collect melting range and IR spectra Notes: Melting range = 50-52 C Percent Yield: 760mg-540mg 760mg = 28.94% Nitration of Piperonal Pre-Lab Notes: Weigh out 150mg of piperonal into beaked Place RBF in warm water bath over magnetic stirrer apparatus Add 5ml of HNO3 into RBF Slowly add piperonal into RBF over 10 minute period Continue to stir for 20 minutes Pour solution into 100ml of ice-cold water Collect crystals via vacuum filtration Recrystallize in warm ethanol Add ethanol solution to ice bath and collect reformed crystals Collect IR Notes: Solution turned yellow to dark red with addition of piperonal When solution was added to cold water a yellow precipitate formed immediately Percent Yield: 1000mg-939mg 1000mg = 61.0% Bromination of Acetanilide Pre-Lab notes: Weigh out 50mg of acetanilide into micro scale tube Add 8 drops of acetic acid to tube Add 6 drops of bromine to tube Stir solution for 10 minutes Add .5ml of water to tube and swirl Cool in ice bath for 5 minutes Collect crystals via vacuum filtration Recrystallize with ethanol Collect IR Notes: While stirring the solution developed orange crystals Solution also turned a rusty-brown color when swirled Percent Yield: 50mg-31mg 50mg = 38.0% Friedel-Crafts Alkylation Pre-Lab Notes: Weigh out 138mg of 1,4-dimethyloxybenzene into a reaction tube Add acetic acid .4ml into tube Add reaction tube into warm water bath Add 200mg of t-amyl alcohol into warm reaction tube Cool in an ice bath and add .4ml of cold sulfuric acid drop wise Stir reaction with glass rod and remove from ice bath and allow solution to warm to room temperature Allow solution to rest for 30 minutes Place solution in ice bath again Slowly add about 2.5ml of water to tube Filter solution and collect crystals Recrystallize solution in hot methanol Collect IR Notes: After adding sulfuric acid to solution created a solid by-product Percent Yield: 140mg-166mg 140mg = 118.57% Isolation of Betulin & Rearrangement to Allobetulin Pre-Lab Notes: Cut out about 500mg of birch bark and continue to cut into the smallest pieces possible Place the bark into a RBF with 15ml of chloroform and some boiling chips Add condenser to apparatus and reflux for 30 minutes Filter hot solution through a Hirsch and funnel wash bark with three 10ml portions of chloroform, adding each wash together with filtered solution Run chloroform solution though silica gel column collect effluent Weigh out about 10mg of Betulin and run a TLC chromatography on this using an eluent of chloroform/acetate (9:1) Dissolve 120mg of p-TSA in the remaining chloroform solution of betulin and 3 drops of water along with a black boiling chip Reflux vigorously for 60 minutes over a water condenser Cool solution and wash with three 25ml portions of sodium bicarbonate Dry solution over anhydrous sodium sulfate Filter solution and Roto-Vap the chloroform solution Collect the dry product and air dry it Collect IR Notes: Percent Yield: 100mg-78mg 100mg = 22% Etherification Reactions Pre-Lab Notes: Weigh out 296mg of cinnamic acid into 5ml RBF Add 4ml of ethyl alcohol to RBF Add 1 drop of sulfuric acid and a black boiling chip to RBF Connect two distillation tube to RBF, pack one with steel wool Bring solution to boil for one hour Cool solution to room temperature and place solution into a 25ml RBF Roto-Vap solution Add 15ml of ether and wash with three 15ml portions of sodium bicarbonate Extract once with 15ml of NaCl solution Filter via vacuum filtration Roto-Vap filtered solution Collect IR Notes: Experiment went according to procedure Percent Yield: 200mg-361mg 200mg = 180.05% N,N-Diethly-m-toluamine (DEET) Pre-Lab Notes: Add 1.37g of toluic acid and 1.5ml of thionyl chloride into a 50ml RBF Add black boiling chip and assemble apparatus Heat for about 20 minutes Cool solution to room temperature and add 16ml of ether Make a mixture of diethylamine (3.5ml) in 8ml of ether and add to dropper funnel Add this mixture slowly to reaction flask over a period of 20 minutes After the addition period, wash the solution with 10ml of sodium hydroxide solution Wash condenser with 6ml of water and add this to NaOH solution Allow layers to separate, add more ether and shake again Wash the ether layer with 10ml NaOH, 10ml HCL, and 10ml of water Dry over anhydrous sodium sulfate and Roto-Vap ether solution Collect IR Notes: Dense white cloud appeared with addition of diethylamine solution Percent Yield: 1460mg-1370mg 1460mg = 94.09% Classification Tests for Aldehydes and Ketones Pre-Lab Notes: DNPH Add 1 drop ethanol to tube along with unknown Add 1 drop of 2,4-dinitrophenylhydrazine reagent Look for yellow or red-orange precipitate Chromic acid Add a drop of unknown and acetone into tube Add reagent Look for green coloration Tollens reagent Add .5ml of A with 1ml of B followed by ammonia solution to dissolve the silver oxide Add unknown dissolved in 2-ethoxyethyl ether Look for mirror formation Iodoform Add one drop unknown to .5ml of dimethoxythane to a test tube Slowly add .75ml of iodine solution in KOH Add 2.5ml of water Look for yellow precipitate Ferric Chloride Add one drop of unknown to .5ml of aqueous ferric chloride Look for a highly colored complex for positive test Aldol Condensation/2D NMR Pre-Lab Notes: Add 12ml of EtOH to a RBF with 120mg of NaOH over a magnetic stirrer Place RBF in salt-ice water bath and stir until dissolved Add 380mg of nitrobenzenealdehyde and stir until dissolved Add 480mg of B-Ionone dissolved in ethanol drop wise over a 30-40 minute period Stir for 90 minutes Filter crystals from solution using vacuum filtration Wash crystals with water and hexane Air dry Recrystallize with ethanol Collect IR Notes: Solution turned yellow with addition of ionone Percent Yield: 815mg-530mg 815mg =65.09% Knoevenagel Condensation Pre-Lab Notes: Add 200mg of NaOH to 15ml of ethanol to flask Mix 480mg of benzyl vanillin to 30mnl ethanol Add 250mg of nitromethane to the cold benzyl vanillin solution and stir until dissolved Add NaOH solution to vanillin solution at a rate of about 5ml/minute while stirring After all NaOH solution is added, mix with ice cold water to dissolve precipitate Pour solution into HCL/Water mixture Stir for 15 minutes Filter out crystals and wash with cold ethanol Collect IR and melting range Notes: White precipitate appeared after NaOH solution was added to reaction Melting range = 102-108 C Percent Yield: 480mg-316mg 480mg = 66.49% Diphenylcyclopropenone Pre-Lab Notes: Stir .3ml of triethylamine in 2ml of methylene chloride Add 560mg of dibromodiphenylacetone in 3ml of methylene chloride over 60 minute time frame Stir solution another 30 minutes after last addition of dibromodiphenylacetone Wash with two 2ml portions of HCL Slowly add 4ml of cold sulfuric acid in 2ml of water Cool solution until pink precipitate forms Collect crystals with funnel, and wash with methylene chloride Add solid precipitate to 1ml of methylene chloride and 2ml of water Slowly add 240mg of sodium carbonate Wash with two 2ml portions of methylene chloride Dry over magnesium sulfate Filter solution and Roto-Vap solution Recrystallize with hot hexane Collect IR Notes: Experiment went according to procedure Percent Yield: 560mg-376mg 560mg = 68.27%

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