In a set of reactions acetic acid yielded a
product D.
SOCI Benzene HCN H.OH
CHCOOH ➝ A ➝ B ➝ C ➝ D
Anly. AICI₃
The structure of D would be:
Answers
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The structure of compound 'D' would be that of 2-hydroxy-2-phenylpropanoic acid [ C6H5C(OH)(CH3)(COOH) ], shown in the image attached below.
(i) CH3COOH + SOCl2 -> CH3COCl [A] + SO2 + HCl
• Acetic acid reacts with thionyl chloride to from acetyl chloride, having the chemical formula CH3COCl.
• Sulphur dioxide gas and hydrogen chloride gas are formed as by-products in the reaction.
(ii) CH3COCl + C6H6 (benzene) + anhydrous AlCl3 -> C6H5COCH3 [B] + HCl + AlCl3
• The above reaction is a Friedel-Crafts acylation reaction.
• In a Friedel-Crafts acylation reaction, an aromatic ring, such as benzene, reacts with an acyl or acid halide (RCOX) in the presence of a Lewis acid such as anhydrous aluminum trichloride (AlCl3), which acts as a catalyst to form a ketone as the final product.
• In the reaction stated above, acetyl chloride (CH3COOH), i.e., compound A reacts with benzene and anhydrous AlCl3 to from acetophenone (C6H5COCH3) as the final product.
(iii) C6H5COCH3 + HCN -> C6H5C(OH)(CN)(CH3) [C]
• Acetophenone reacts with hydrogen cyanide to form 2-hydroxy-2-phenylpropanenitrile, represented as C6H5C(OH)(CN)(CH3).
(iv) C6H5C(OH)(CN)(CH3) + H2O -> C6H5C(OH)(COOH)(CH3) [D]
• On adding water to 2-hydroxy-2-phenylpropanenitrile, it undergoes hydrolysis to form an acid named 2-hydroxy-2-phenylpropanoic acid.
• The C-CN bond is broken by the water molecule and a COOH bond is formed. The structure of 'D' is shown in the image attached below.
