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In the preparation of benzocaine, why is the ester washed with 2m of sodium carbonate? With references
Accepted Answer
The 2M sodium carbonate wash in benzocaine synthesis is crucial for removing impurities and unwanted byproducts. Here's why:
1. Neutralization of Acidic Byproducts: Benzocaine synthesis often involves acidic byproducts like benzoic acid. Sodium carbonate, a base, neutralizes these acids, converting them to their sodium salts, which are soluble in water and easily removed by washing.
2. Hydrolysis of Unreacted Acid Chloride: If the reaction involves an acid chloride, sodium carbonate can hydrolyze any unreacted acid chloride, preventing it from contaminating the final product.
3. Removal of Excess Acid: Even if the synthesis doesn't produce significant acidic byproducts, a wash with sodium carbonate can help remove any excess acid used in the reaction, ensuring a purer final product.
References:
Organic Chemistry, 10th Edition by Paula Yurkanis Bruice
Vogel's Textbook of Practical Organic Chemistry by Brian S. Furniss, Antony J. Hannaford, Peter W. G. Smith, and Austin R. Tatchell
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