Question

Step 1: Synthesis of 2-methoxy-6-(p-tolyliminomethyl)-phenol: Imine formation Weigh a 250 mL beaker and then add 0.76 grams (5 mmol) of ortho-vanillin to one side of the beaker. Record the total mass of the beaker plus the ortho-vanillin. Using weighing paper, accurately weigh an equivalent amount of para-toluidine (0.535 grams, 5 mmol) and add this to the opposite side of the beaker. Using a heavy glass stirring rod, mix and grind the solids together until they become a homogeneous dry powder (If the starting materials are pre-crushed, the powder forms in about three minutes - If not pre-crushed, it takes about 15 minutes). Record all observations and explain what is occurring in the reaction. Weigh the beaker and record the mass. Determine the percent yield. Remove a small sample of this material for IR analysis and melting point. Compare the features of your spectrum with those of the starting materials. Identify the absorption peak for the CNN stretch, and suggest a reason why the frequency is lower than expected. Step 2: Synthesis of N-(2-hydroxy-3-methyoxybenzyl)-p-methylaniline: Reduction of the imine Add about 15 mL of 95% ethanol to the beaker containing your imine product and stir the mixture to partially dissolve the amine. Weigh out about 0.1 g sodium borohydride and slowly add this to the beaker in small increments with continued stirring. Record all observations and explain what is occurring in the reaction. Step 3: Synthesis of N-(2-hydroxy-3-methyoxybenzyl)-N-p-tolylacetamide: Acetylation of the imine Add 2 mL of glacial acetic acid (concentration = 17.4 M) to the amine to destroy the excess borohydride and to neutralize the phenoxide ion. Add 2 mL of acetic anhydride and a boiling chip and warm the solution in a beaker of boiling water for 5-10 minutes. Move this beaker to a stir plate, and stir the solution fairly rapidly while slowly adding 75 mL water. Continued stirring should leach out the alcohol and acetic acid causing the amide product to precipitate. Cool the mixture in an ice bath and collect the white solid by vacuum filtration, pulling air through for several minutes to evaporate most of the water. Weight the product, and analyze by IR spectroscopy and melting point.
What is the theorectical yeild for step 1 and step 3?

- Step 1 has 0.76g of ortho-vanillin and 0.535g of para-toludine.

-step 3 has 2ml of glacial acetic acid and 2ml of acetic anhydride. it gets warms and 75ml of water is added

Answer 1

step. I octhy HP M. f. Cg H803 152 gm phenst 244 gm. SNg o vanillin 2 methoxy-6CP togtioinomethyt) M. f - GEHISNO Theoretical field 152 gem o-vanilin = 241 go q amethonyol Ptoly liminomethy!) phenol 0.76 gm = x gro x gm = 241 X 0.76 gm seg 152 ghe = 1.205 gm Theoretical gield Ce) - Lidos gm

step-08 (* hyaranya melegbewegt) methyl aniline N(2 hydroxy 3 methyl benyl N-p.tolyl acetamide. 11 - ody u m.f. Gothing M. ad 243 gm о M.F. G7 Hig Noz M.4. - 285 gm Theoretical gield Den 243 gm A = 285 gm q B compound compound. I gm q A = xe gro q B. x gm q B = 285 gm x f gm 243 gm Note Hors = 1.47 gm Theoretical field - 1.17 gm In second steps 1.215 gm q N(2 hydboky a methoxybenyl) p.methyl aniline product us formed. If out of these. & gm B used to step III then theoretical field is the t.17 gm.

If all the quantity 1.215 gm formed in second step & used to Step. III then theoretical field is the ди on Mf. - Gg H17 NO2 onut = 243 gm M. f - G7 HigNO₃ Mint = 285 gm Theoretical yield- 243 gm A 1.215 gm = 285 go. B = x gm B 285 × 1.215 gm 243 gm = 1.425 gm Theoretical field = 1425 gm