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(ORGANIC CHEM LAB 2) SYNTHESIS OF ACETAMIDES 1. A CHM 211 student used three times the...

(ORGANIC CHEM LAB 2) SYNTHESIS OF ACETAMIDES

1. A CHM 211 student used three times the specified amount of hydrochloric acid in step # 1, but otherwise followed the above procedure. The student obtained no product. Explain why. (STEP 1: Weigh 1.0 g of unknown amine and add to a 100 mL Erlenmeyer flask. Add 28 mL of water and 1.0 mL of concentrated hydrochloric acid to the Erlenmeyer flask.)

2. The student ran the reaction again. This time took a one-hour break after adding the acetic anhydride but before adding the sodium acetate solution. (ORIGINAL TIME WAS 10 MINUTES) The student obtained no product. Explain, with chemical equations and/or formulas, what went wrong?

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Answer #1

(1) Since excess HCl is used, it will hydrolyze acetamide. So no product will be obtained.

(2)

Since the product is present in the reaction mixture for long time, it will be hydrolyzed in the acidic medium. So no product will be obtained. Sodium acetate will provide acetate ions which will combine with excess protons to form acetic acid which is feebly ionised. So the acidity of the reaction mixture is controlled.

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