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Acetanilide Synthesis: Yield Calculations

The limiting reagent in the reaction between aniline and acetic anhydride is aniline, as it produces less acetanilide compared to the excess acetic anhydride. The theoretical yield of acetanilide is calculated to be 4.35 g. The percent yield based on the actual yield of 3.30 g is 75.86%.

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15 views2 pages

Acetanilide Synthesis: Yield Calculations

The limiting reagent in the reaction between aniline and acetic anhydride is aniline, as it produces less acetanilide compared to the excess acetic anhydride. The theoretical yield of acetanilide is calculated to be 4.35 g. The percent yield based on the actual yield of 3.30 g is 75.86%.

Uploaded by

Jeev
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
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Answer on Question #58182 – Chemistry – Organic Chemistry

Task:
Assume that 3.0 g of aniline and 4.5 mL of acetic anhydride (density ρ = 1.08 g mL-1) are used in
the preparation of acetanilide.
1) What is the limiting reagent? Justify your answer.
2) What is the theoretical yield in grams of acetanilide?
3) What is the % yield if 3.30 g of acetanilide are obtained?

Solution:
We write the reaction of interaction the aniline with acetic anhydride to form acetanilide:

H
NH2 O O N CH3

+ H3C O CH3 O + CH3COOH


aniline
acetic anhydride acetanilide acetic acid

We find the molar mass of aniline and acetic anhydride:

g
M  aniline   M  C6 H 5 NH 2   12  6  1 7  14 1  93( );
mol
g
M (acetic anhydride)  M (C4 H 6O3 )  12  4  1 6  16  3  102( ).
mol

Convert each substance to moles:

m(C6 H 5 NH 2 ) 3g
n  aniline     0.0322mol;
M  C6 H 5 NH 2  93 g
mol
g
m(C4 H 6O3 )  (C4 H 6O3 )  V (C4 H 6O3 ) 1.08 ml  4.5ml
n(C4 H 6O3 )     0.0476mol
M (C4 H 6O3 ) M (C4 H 6O3 ) 102 g
mol

1) To find the limiting reagent, take the moles of each substance and divide it by the coefficient
of the balanced equation. The substance that has the smallest answer is the limiting reagent.

Determine the limiting reagent:


For aniline: 0.0322 / 1 = 0.0322
For acetic anhydride: 0.0467 / 1 = 0.0476.

There is enough acetic anhydride to produce 0.0467 mol acetanilide, but only enough aniline to
produce 0.0322 mol acetanilide. This means that the amount of acetanilide actually produced is
limited by the aniline, which is therefore the limiting reagent.
Answer:
Limiting reagent is aniline.

2) Aniline and acetanilide stand in a one-to-one molar relationship, so 0.0322 mol of aniline
produces 0.0322 mol of acetanilide. The amount of acetic anhydride does not play a role, since
it is in excess.
Then,

n  aniline   n(aceta n ilide)  0.0322mol.

We find the molar mass of acetanilide:

M (aceta n ilide)  M (C8 H 9 NO)  12  8  1 9  14 1  16 1  135( g ).


mol

We find the theoretical yield in grams of acetanilide:

m(aceta n ilide)  n(C8 H 9 NO)  M (C8 H 9 NO)  0.0322mol 135 g  4.347 g  4.35 g.
mol

Answer:
The theoretical yield of acetanilide is 4.35g.

3) What is the % yield if 3.30 g of acetanilide are obtained?


Theoretical yield: 4.35g.
Actual yield: 3.30g.

Percent yield (%Yield):

Actual Yield  mass or moles 


% Yield  100% .
Theoretical Yield  mass or moles 

Then,

Actual Yield 3.30 g


Percent Yield  100%  100%  75.86%.
Theoretical Yield 4.35 g

Answer:
Percent yield of acetanilide is 75.86%.

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