Nitration of 2-Benzylpyridine Determine the theoretical yield of the product. Pr

Question

Nitration of 2-Benzylpyridine

Determine the theoretical yield of the product.

Procedure:

This procedure is to be done in subdued light. Transfer 5 mL of concentrated H2SO4 (90 mmol) into a 25 mL Erlenmeyer flask. Cool the acid to below 5oC in an ice bath. Swirl the flask in the ice bath while adding 2-benzylpyridine (1.0 mL, 6.2 mmol). While continuing to swirl the solution in the ice bath, add concentrated nitric acid (1.0 mL, 16 mmol) dropwise over about 2-3 minutes. Record observations made during this addition. Heat the resulting mixture to about 80oC in a shallow water bath for 20 minutes.* Transfer the reaction mixture onto 80 g of crushed ice in a large beaker (>400 mL). From our ice maker, this comes to 15-18 pieces. The small flask may be rinsed with a small amount of water. Make this mixture basic by the careful addition of the NaOH solution. Record observations made during this process. Confirm that the solution is significantly basic (>11) by the use of a pH test strip. If the mixture is still warm by this time, add a few more pieces of ice. Add diethyl ether (about 75 mL) and stir for about 10 minutes to extract your product. Separate the layers carefully by the use of a separatory funnel. Dry the ether layer (top) using MgSO4 or CaSO4. Decant this solution into a tared round bottom flask and remove the ether via rotary evaporation. Recrystallize the residue using ethanol (approx. 10 mL ethanol per gram). Collect the product on a Hirsch funnel.

Explanation / Answer

2-benzyl pyridine MWt = 169.23, mmol = 6.2 mmol

Product MWt = 259.22

Theoretical yield in grams = (2-benzyl pyridine mmol X Product MWt)/1000 = (6.2 x 259.22)/1000 = 1.607 g

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