CALCULATION OF YIELDS

When calculating yields in organic chemistry, you must be aware of the difference between calculations
of mass recovery and calculations of isolated yield.

Mass recovery calculations are used when the starting material and the isolated material are the same
chemical compound. In other words, when comparing starting material to the isolated material, no new
bonds were formed or broken, and obviously no changes to the molar mass occurred. An example is the
isolation of N-phenylacetamide from a mixture containing salicylic acid (this was done in Experiment #2).

Calculation of % mass recovery of N-phenylacetamide:

For example, a student has 2.00g of a mixture that contains mostly N-phenylacetamide with a minor
impurity of salicylic acid. The amount of the salicylic acid impurity is 10% m/m [ m/m means mass of
salicylic acid/ mass of total sample]. How much mass of salicylic acid is in this sample? How much N-
phenylacetamide is in this sample? You should be able to calculate that there is 0.200g of salicylic acid
and 1.800g of N-phenylacetamide in this sample. Also, if we were to recrystallize this sample, the
maximum amount of N-phenylacetamide that is theoretically recoverable would be 1.80g. If after
recrystallizing, 0.600g of N-phenylacetamide is obtained, the % mass recovery of N-phenyacetamide
would be 33.3%.

Isolated yield calculations are used when the starting material is involved in a chemical reaction and
results in the formation of a new chemical compound called the product. A chemical reaction on the starting
material can result in bonds been broken and formed and result in a product that has a different molar
mass. Due to the changes in molar mass between starting material and product, we simply cannot directly
use mass only (as was done in mass recovery calculations), we have to take into account the molar masses
of both the starting material and the product, and the concept of the mole. To better understand isolated
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yield calculations, the three terms of yield, theoretical yield and percentage isolated yield are discussed
next.

The yield of a product is simply the amount of product obtained in an experiment. Yield is expressed
in grams.

The theoretical yield is the amount of product in grams that could be obtained under ideal conditions
where all of the reactant is converted to product. When this happens, chemists say that the reaction
proceeded with 100% conversion. In practice, organic reactions rarely give the theoretically possible yield.

The percentage isolated yield (% isolated yield) is the ratio of the actual amount of product obtained
in grams divided by the theoretical yield possible in grams, and this ratio is expressed as a percentage.
Notice that the units of grams cancels out and the answer, which is expressed as a percentage, is without
units.

Theoretical Yield

The theoretical yield is calculated from the balanced equation for the reaction and the known quantities
of starting materials (reactants). For example, consider the conversion of trans-cinnamic acid to methyl
trans-cinnamate. The balanced equation for this chemical reaction is given below.

This balanced equation tells us that under ideal conditions:

In an actual experiment the best results are not always obtained by using the reagents in the proportions
indicated by the equation for the reaction. It may be better to use an excess of one of the reactants.

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 When the reactants are not used in the molar proportions dictated by the equation, then, as the reaction
proceeds, one of the reactants will be completely consumed while there are still some of the other reactants
left. The reactant that is used up first and causes the reaction to stop is called the limiting reagent.

To determine the theoretical yield of a reaction it is first necessary to determine the limiting reagent.
Suppose that in the above reaction 1.200 grams of trans-cinnamic acid was reacted with 20 mL of methanol.
To determine which of these two reactants is used up first (limiting reagent), you must first determine the
number of moles of each reactant.

The balanced equation for this reaction tells you that under ideal conditions the ratio of moles of trans-
cinnamic acid to moles of methanol is 1:1. There is excess methanol. Therefore, in this case the trans-
cinnamic acid is the limiting reagent. Once the limiting reagent is determined the theoretical yield can be
calculated from the expression:

Theoretical yield = (moles of limiting reagent) (ratio) (molar mass of product)

The "ratio", in this expression is the stoichiometric ratio of product to limiting reagent. One mole of trans-
cinnamic acid, under ideal circumstances, would yield one mole of methyl trans-cinnamate. Using one of
the two methods shown below we can calculate the theoretical yield of methyl trans-cinnamate.

Method 1

1 mole cinnamic acid yields one mole methyl trans-cinnamate

0.008099 mole cinnamic acid therefore should yield 0.008099 mole methyl trans-cinnamate

Molar mass of methyl trans-cinnamate = 162.19 g.mole-1

Mass of 0.008099 mole of methyl trans-cinnamate = moles × molar mass

= 0.008099 mol × 162.19 g.mole-1 = 1.314 g

Theoretical yield of methyl cinnamate = 1.314 g

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Method 2

Percentage Isolated Yield of methyl trans-cinnamate

Suppose that in the above example the actual yield was 0.983 grams of methyl-trans-cinnamate