About Percent Yield in the Organic Laboratory

Definitions: Theoretical Yield: The maximum amount of product if ALL of the limiting reagent
reacted exactly as described by the balanced equation, with no losses due to
side reactions or spillage.

Percent Yield: The amount of purified product obtained, divided by the theoretical yield.
A Percent Yield over 100% is physically impossible -- as far as we know, you cannot create
matter...if you do, please let your instructor know right away so we can nominate you for
the next Nobel Prize in chemistry!!

Crude Percent Yield: Percent yield of the crude product before purification. This crude
material may contain product, starting material, byproducts from side reactions, moisture,
and a variety of other impurities. Therefore this number may be over 100%. The amounts
of such impurities are more characteristic of the technical details of the operation or the
technical skill level of the operator than the nature of the reaction itself, so this number
is rarely published in the chemical literature.

Purified Percent Yield: See Percent Yield. These are the same. If the chemical literature
refers to percent yield,without stating "purified", it is assumed that the product was pure.

Percent Recovery: This describes the efficiency of purification operations such as

recrystallization, where the identity of the material is the same before and after the operation.
To calculate, divide the amount obtained by the amount which entered the operation, times 100
to express in percent. The molecular weight doesn't change, so units of grams may be used.

How to calculate: First calculate the theoretical yield, then use it in the other calculations.
(LR = limiting reagent, P = product, MW = molecular weight in g/mol)

amount actually used in reaction, in moles

moles of P
Theoretical yield (g) = (amount of LR)•(MW of P)•
moles of LR

stoichiometric ratio from

balanced equation
(for many organic
this is the amount of reactions this is 1:1 )
purified product obtained

amount of P (g)
Percent yield = purified percent yield = •100
theoretical yield (g)

amount of crude P before purification (g)

Crude percent yield = •100
theoretical yield (g)

Complicated balanced equations are uncommon in organic chemistry. Many organic reactions have a
stoichiometry of 1:1 in the balanced equation. In this case the calculation can be further simplified; the
theoretical yield calculation may be skipped. But the amounts must still be converted to moles!

amount of P (mol)
Percent yield (if stoichiometry is 1:1) = •100
amount of LR (mol)
Yield Calculations: Example
Arthur Rytis prepared acetaminophen in the Organic Lab. Starting with 2.14 g of p-aminophenol, and 1.9 mL
acetic anhydride, Arthur obtained 3.22 g crude product. After setting aside a sample of the crude product for
TLC analysis, Arthur purified 2.88 g of the crude product by recrystallization. Note that not all of the crude
product was recrystallized; the fraction used was 2.88/3.22 = 0.894. The recrystallized product weighed 2.43 g.

Balance the equation: H

NH2 N
O O O
+ +
O
HO O HO HO
1 C6H7NO 1 C4H6O3 1 C8H9NO2 1 C2H4O2

The stoichiometry here is 1:1: 1 mol of limiting reagent gives 1 mol product

Find the limiting reagent: Since this balanced reaction has a 1:1 stoichiometry, the limiting reagent
is simply the lower amount (in moles) of these two compounds

for p-aminophenol, for acetic anhydride,

2.14 g (1.9 mL)•(1.08 g/mL)

= 0.0196 mol = 0.0201 mol
109 g/mol 102 g/mol
(note that the density is used to convert
the volume of acetic anhydride to mass)

so, p-aminophenol is the limiting reagent (LR) MW of P

gP moles of P
Calculate theoretical yield: Theoretical yield (g) = (moles of LR)• •
mole P moles of LR

1
= (0.0196 mol)•(151 g/mol)• = 2.96 g
1

Calculate Percent Yield: Since not all of the crude product was recrystallized, we need to account for that in the
calculation of percent yield. In other words, the percent yield should reflect what you would have gotten if you
purified the whole batch. Calculate in the usual way, then divide by the fraction used for recrystallization.

2.43 g
Percent yield = •100 / 0.894 = 92%
2.96 g
dividing by the fraction used in the recrystallization

An alternative way to calculate this, when not all the crude is purified, is to consider the formation of crude
product and purification to be individual steps, then the overall yield is obtained by multiplying the yields of the
two steps. This method also accounts for the fact that only a fraction was used for recrystallization.

3.22 g
Crude percent yield = •100 = 109%
2.96 g

2.43 g
Percent recovery from recrystallization = •100 = 84%
2.88 g

Percent yield = 1.09•0.84•100 = 92% (this is the same answer obtained above)