Why does only the amino group react in the synthesis of paracetamol?

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In summary, when 4-aminophenol reacts with an acyl chloride or acid anhydride, only the R-NH2 group reacts due to its higher nucleophilicity compared to the R-OH group. This is because the phenolate anion, which is a better nucleophile than free phenol hydroxyl, is not present in significant amounts to interfere with the reaction. Under strongly basic conditions, the phenolate ester formed can also act as an electrophilic species and will be amidated by the amino group attack on the ester carbonyl, preventing the formation of any significant amount of ester.
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jsmith613
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I was reading through my textbook and apparently when 4-aminophenol reacts with an acyl chlordie / acid anhydride (as in the synthesis of paracetamol) only the R-NH2 group reacts and NOT the R-OH group.

Why is this?
 
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The amino group is considered more nucleophilic to attacking the acyl group and displacing chloride, than a phenolic hydroxyl. The phenolate anion will not be present in enough quantity to interefere (it is somewhat better nucleophile than free phenol hydroxyl).

Of the phenolate ester that is formed under strongly basic conditions, it is also a good electrophilic species like the acyl chloride, and is amidated by the amino group attack on the ester carbonyl releasing the phenolate anion. One wouldn't expect to see much if any ester as a result.
 

What is aminophenol with R-COCl?

Aminophenol with R-COCl is a chemical compound that is formed when aminophenol, an organic compound with a benzene ring and an amino group, reacts with an acid chloride, denoted as R-COCl. This reaction results in the formation of an amide compound.

What is the chemical structure of aminophenol with R-COCl?

The chemical structure of aminophenol with R-COCl can be represented as C6H5NHCOR, where R represents the organic group attached to the amide functional group.

What is the purpose of using aminophenol with R-COCl in scientific research?

Aminophenol with R-COCl is commonly used as a reagent in organic synthesis reactions, specifically in the formation of amide bonds. It is also used in the production of pharmaceuticals, dyes, and other chemical compounds.

What safety precautions should be taken when handling aminophenol with R-COCl?

Aminophenol with R-COCl is a hazardous chemical and should be handled with caution. It is important to wear appropriate personal protective equipment, such as gloves and goggles, and to work in a well-ventilated area. In case of skin or eye contact, immediately rinse with water and seek medical attention.

Are there any potential health hazards associated with exposure to aminophenol with R-COCl?

Yes, exposure to aminophenol with R-COCl may cause irritation to the skin, eyes, and respiratory system. Prolonged or repeated exposure may also cause more serious health effects. It is important to follow proper safety protocols and guidelines when working with this chemical compound.

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