Calculate the yield of 4-bromo-2-chloroacetanilide. Chlorine gas is generated in

Question

Calculate the yield of 4-bromo-2-chloroacetanilide. Chlorine gas is generated in situ from HCI and NaCLO_3 in an oxidation-reduction reaction. What compound is oxidized and what compound is reduced? Write balanced, half reactions for the oxidation and the reduction reactions. If less than this amount is available, recalculate the amounts of all as reagents that should be used in the next procedure. Assign the important bands in the IR spectrum that verify the product identity. Wear eye protection at all times in the laboratory. HCI is a strong acid. Wear gloves when handling it. If comes in contact with your skin. HCI is a strong acid. Wear gloves when handling it. If HCl protection in the laboratory. your skin, wash off with lots of cold running water. The 50% NaOH solution is very caustic. Wear gloves at all times. Clean up any spills immediately. Into as-mL round-bottom flash fitted with a reflux condenser and a magnetic stirrer of 4.1 g of bromo-2- chloroacetanilide 7 mL of 95% ethanol, and mL concentrated HCI Heat the solution with stirring, to a gentle boil, using a heating mantle as the add source. Reflux for at least 1 hour. The solid will dissolve into a clear solution as it is heated, and then a white precipitate will form. Heat 26 ml of water on a hot plate. Pour the hot water into the reaction mixture and swirl the flask to redissolve the solid. Pour the reaction mixture onto 50 g of ice. While stirring, a 4 mLof50% sodium hydroxide solution. Use pH paper to check the pH of the solution. If the pH is still acidic, add a little more NaOH until the stirred solution is basic to litmus paper. Collect the crude product by suction filtration, washing well with cold water. The product may be recrystallized from hexanes. Dry in air. Do not use a drying oven. Record the weight.

Explanation / Answer

Preparation of 4-bromo-2-chloroacetanilide

1. Theoretical yield of product : 4-bromo-2-chloroacetanilide

molar mass of 4-bromoacetanilide = 214.062 g/mol

molar mass of 4-bromo-2-chloroacetanilide = 248.504 g/mol

Theoretical yield = 3.614 g x 248.504/214.062

                          = 4.195 g (100%)

Actual yield = 3.262 g

Percent yield = 3.262 g x 100/4.195

                      = 77.76%

3. Required mass of product = 4.1 g

We would need

4-bromoacetanilide = 3.614 x 4.1/3.262 = 4.542 g

95% ethanol = 4.1 x 7/3.614 = 7.94 ml

HCl = 4.3 x 4.1/3.614 = 4.9 ml

50% NaOH = 4 x 4.1/3.614 = 4.54 ml

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