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What can cause a low percent yield? In lab we did fischer esterification using benzoic acid...

What can cause a low percent yield? In lab we did fischer esterification using benzoic acid and methanol to yield methyl benzoate. 3.05 grams of benzoic acid were used and 1.10 grams of methyl benzoate were produced. We also washed the product multiple times with water, 10% sodium bicarbonate solution, then saturated sodium chloride solution. Could the washing cause a low percent yield? If so, can you explain why?

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Usually, percent yield is lower than 100% because the actual yield is often less than the theoretical value. Reasons for this can include incomplete or competing reactions and loss of sample during recovery. ... This can happen when other reactions were occurring that also formed the product.

In the case of esterification, when we were doing the washing the impurities from the compound were removed which cause an decrease in weight of product as many time we will do washing some how weight will decrease it cause an decrease in yield but an increase in purity

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