Question

Multistep Synthesis: Synthesis of Amine (Organic Chemistry Lab)

Question

1. Explain each step of reaction mechanism. (How does it work?)

2. Discuss reason for reaction sequence. (Why must one reaction occur before another?)

3. Explain how IR supports the major product.

Experiment Procedure

Imine Formation:

  1. Weigh a 20 mL beaker and then add 380 mg of ortho-vanillin and 268 mg of para-toluidine. Care should be taken to add equivalent molar amounts of the two reactants.

  2. Observe the mixture and record your observations.

  3. Mix the solids thoroughly with a glass rod. Record any observations. Continue to mix the solids until they become a homogeneous dry powder.

  4. Weigh the beaker and product and determine the percent yield. Remove a small sample for an IR and meting point determination.

Note: If the reaction product does not become a powder, then recrystallize the product from hexanes and isolate before continuing to the next reaction

Reduction of Imine:

  1. Add about 8 mL of 95% ethanol to the beaker containing the imine product and stir the mixture to partially dissolve the imine.

  2. In small increments, slowly add 49 mg of sodium borohydride to the solution with continued stirring.

  3. Record all your observations

Acetylation of the Amine:

8. Carefully add 1 mL of glacial acetic acid to the amine to destroy any excess borohydride and neutralize the phenoxide ion.

9. Add 1 mL of acetic anhydride and gently heat the solution with stirring for approximately 10 minutes.

  1. Allow the solution to cool and then carefully transfer to a larger beaker.

  2. Slowly add 40 mL of water with gently stirring with glass rod. Continue to gently stir the solution to precipitate the amide product.

  3. Cool the mixture in a ice bath and collect the solid by vacuum filtration. Due to the volume, it will be necessary to perform the vacuum filtration in two portions and then combine the isolate products.

  4. If completed in one day, allow the product to air-dry overnight. Once dry, weigh the product and determine its melting point.

  5. Recrystallize the product from a minimal quantity of hexanes.

  6. Weigh the recrystallized product and determine the melting point. Submit 5-10 mg of the product for an IR.

Experiment Result

IR spectra

寸 3500 2500 Wavenumber (cm-1) 3000 1000 2000 1500

0 0
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Answer #1

NT OCH 268 380 OCH Amine. Producb The amideCa 4

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