15 grams of Adipic acid is treated with excess thionyl chloride, and the resulti

Question

15 grams of Adipic acid is treated with excess thionyl chloride, and the resulting acid dichloride is reacted with 20mL butyl amine (density=0.74 g/mL). After work up and recrystallization, 12.5 g of N,N'-dibutyl adipamide is obtained. What is the limiting reagent and percent yield?

Explanation / Answer

You can calculate the theoretical yield of the product based on the original mass of adipic acid. You'll need to look at the equations, but I'm guessing there is a 2:1 relationship between moles of adipic acid and your amide product. So, grams adipic acid --> moles adipic acid --> moles product --> grams product. Then, calculate moles of butyl amine. Volume X density = grams --> moles dibutyl amine --> moles product --> grams product. Between those two, the one which gives you the smaller mass of product is your limiting reactant, and the mass of product would be your theoretical yield. Dividing 12.5 grams by the theoretical yield, and multiplying by 100 will give you the % yield.

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