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Preparation of Paracetamol Post Lab

The document summarizes the results of preparing paracetamol: 1) The crude yield was 0.77g and the recrystallized yield was 0.49g. 2) TLC analysis indicated the sample was impure and contaminated with starting material. 3) The melting point and IR spectrum matched that of paracetamol.

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346 views5 pages

Preparation of Paracetamol Post Lab

The document summarizes the results of preparing paracetamol: 1) The crude yield was 0.77g and the recrystallized yield was 0.49g. 2) TLC analysis indicated the sample was impure and contaminated with starting material. 3) The melting point and IR spectrum matched that of paracetamol.

Uploaded by

shmesa_alr
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Sa17582

Preparation of paracetamol post-lab

 Yield of crude = weight of watch glass with sample - weight of watch glass
= 35.72 – 34.95
= 0.77 g

 Recrystallised yield = weight of vial – weight of vial with sample


= 13.54 – 13.05
= 0.49 g

 TLC plate appearance:

There are two spots for the sample (E) in each time interval (2 minutes, 4
minutes, 8 minutes) indicating that the sample is not pure and that it is
contaminated with the starting material. This can be concluded because 4-
aminophenol and paracetamol travel up the plate at different rates due to
their different structures.

 Product melting point:


168.1-170.5 °C

 Product IR spectrum:

Answers:

1. Percentage yield of product

C6H7NO + C4H6O3  C8H9NO2 + C2H4O2


4-aminophenol + acetic anhydrate  paracetamol + acetic acid
𝑎𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
 Percentage yield = x 100
𝑡ℎ𝑒𝑜𝑟𝑖𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑

Actual yield (paracetamol) = 0.77 g

𝑚𝑎𝑠𝑠 (4−𝑎𝑚𝑖𝑛𝑜𝑝ℎ𝑒𝑛𝑜𝑙)
Number of moles (4-aminophenol) =
𝑚𝑜𝑙𝑎𝑟 𝑚𝑎𝑠𝑠

1.1 𝑔
= = 0.01008 mol
109.128 𝑔/𝑚𝑜𝑙

Therefore, number of moles of paracetamol = 0.01008 mol


because of the 1:1 ratio

Theoretical yield = mass (paracetamol)


= number of moles x molar mass
= 0.01008 mol x 151.165 g/mol
= 1.524 g

𝑎𝑐𝑡𝑢𝑎𝑙 𝑦𝑖𝑒𝑙𝑑
Percentage yield = x 100
𝑡ℎ𝑒𝑜𝑟𝑖𝑡𝑖𝑐𝑎𝑙 𝑦𝑖𝑒𝑙𝑑

0.77 𝑔
= x 100
1.524 𝑔

= 50.52 %

 The value is slightly less than the expected because:


- the product was either lost due to spillage or transfer from filter
paper to the watch glass.
- 4-aminophenol or acetic anhydride might have been in excess in
the reaction.
- Some of the product remained in the beaker/ conical flask/ filter
paper.
2. Percentage yield for recrystallisation

 % yield of the recrystalised relative to the crude:

 The crude relative to starting material


yield of recrystalised product = 0.49 g
yield of crude product relative to starting material = 1.524 g

𝑦𝑖𝑒𝑙𝑑 𝑜𝑓 𝑟𝑒𝑐𝑟𝑦𝑠𝑡𝑎𝑙𝑙𝑖𝑠𝑎𝑡𝑖𝑜𝑛
Percentage yield = x 100
𝑦𝑖𝑒𝑙𝑑 𝑜𝑓 𝑐𝑟𝑢𝑑𝑒 𝑟𝑒𝑙𝑎𝑡𝑖𝑣𝑒 𝑡𝑜 𝑠𝑡𝑎𝑟𝑡𝑖𝑛𝑔 𝑚𝑎𝑡𝑒𝑟𝑖𝑎𝑙

0.49𝑔
= x 100
1.524𝑔

= 32.15 %

 The crude relative to the pure


Yield of recrystalised product = 0.49 g
Yield of crude product relative to pure = 0.77 g

𝑦𝑖𝑒𝑙𝑑 𝑜𝑓 𝑟𝑒𝑐𝑟𝑦𝑠𝑡𝑎𝑙𝑙𝑖𝑠𝑎𝑡𝑖𝑜𝑛
Percentage yield = x 100
𝑦𝑖𝑒𝑙𝑑 𝑜𝑓 𝑐𝑟𝑢𝑑𝑒 𝑟𝑒𝑙𝑎𝑡𝑖𝑣𝑒 𝑡𝑜 𝑝𝑢𝑟𝑒

0.49𝑔
= x 100
0.77𝑔

= 63.64 %
3.

Mechanism:

- The lone pair of electrons on the amine group in 4-


aminophenol attacks the carbonyl group (C=O) of acetic
anhydride, which leads to the breaking of the C=O bond.
The nitrogen atom of the amine group then loses a
hydrogen atom(proton) and the bond between the carbon
atom attached to 4-aminophenol and oxygen that was
adjacent to the lost hydrogen atom, regains an electron.
This results in the breaking of the other C-O bond.
Paracetamol is produced, and acetic acid is formed as a by-
product.
- Acetic acid (CH3COOH) dissociates into H+ ions and
CH3COO-. The nitrogen atom of the amine group gains the
H+, thus forming an ionic substance, increasing its solubility.

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