Chemical Reaction: Synthesis of Acetanilide

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Sophomore (College 2nd year) ・Chemistry ・MLA

a. Acetic acid is introduced as a solvent and prevents the occurrence of unwanted substitution reactions.
b. Water acts as a solvent of acetanilide seeing that it is unreactive with the compound. Similarly, since water has a lower boiling factor (100C) compared to the melting point acetanilide (110.50C), it would effortlessly evaporate when heated leaving behind acetanilide during recrystallization. Also, water is favored since it can be able to dissolve a lot of acetanilide whilst hot and allow a lot of it when cooled seeing that it dissolves only a small amount when cool. It will be effortless to obtain dry crystals since water is moderately volatile therefore much of it evaporates.
c. Since charcoal is carbon, it is used as an activator in this reaction. When carbon is added in this reaction, the temperature of the reacting solutions raises and may result in frothing. The charcoal also assists in adsorbing the colored impurities and polymeric to avoid contamination of the end product.
1. Acetic anhydride is more reactive than acetic acid, therefore; there will be better yields. This is because only half the water is formed per mole, thus, favoring the forward reaction. In case acetic acid is used, more water will be formed, and reverse reaction will be favored leading to the formation of esters.
2. Pyridine and 30 amines are weak bases and are used as a nucleophilic catalyst in the reaction.
3. Monoacylation requires the only electrophilic substitution of the arenes and acyl chlorides or anhydrides to occur while for diacylation, the product formed during the first substitution must be activated to allow the reaction to undergo a second substitution. A catalyst such as a Lewis acid catalyst must be present.
4. a. N, N-diphenylacetamide, and acetic acid
b. Acetic acid
c. Acetophenone and acetic acid
d. P-methylacetophenone
e. Ethyl acetate and acetic acid

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