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Acyl Substitution Revisited

Question

Which of the following methods are used for the conversion of carboxylic acids into acid chlorides $(R C O O H ⟶ R C O C l)$ ?
$R C O O H + S O C l_{2} ⟶$
$R C O O H + P C l_{5} ⟶$
$R C O O H + C l_{2} ⟶$
$R C O O H + P + C l_{2} ⟶$

A

R C O O H + C l_{2} ⟶

B

R C O O H + P + C l_{2} ⟶

C

R C O O H + P C l_{5} ⟶

D

R C O O H + S O C l_{2} ⟶

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Solution

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Acid chlorides are prepared by replacing the corresponding hydroxy substituents of carboxylic acid with chlorides. Thus, carboxylic acids can be treated with thionyl chloride $(S O C l_{2})$ , phosphorus trichloride $(P C l_{3})$ , or phosphorus pentachloride $(P C l_{5})$ . But chlorine $(C l_{2})$ can not directly replace $- O H$ .

$R C O O H + S O C l_{2} \to R C O C l + S O_{2} + H C l$

$3 R C O O H + P C l_{3} \to 3 R C O C l + H_{3} P O_{3}$

$R C O O H + P C l_{5} \to R C O C l + P O C l_{3} + H C l$

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