Salicylic acid can be synthesised from phenol. One of the steps in this synthesis is the electrophilic substitution reaction of carbon dioxide with the phenoxide ion, $$$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}$$$. Complete the mechanism in Fig. 9.3 for the reaction of $$$\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}^{-}$$$with $$$\mathrm{CO}_{2}$$$. Include all relevant curly arrows, dipoles and charges. Draw the structure of the organic intermediate.

Chemistry

IGCSE&ALevel

CAIE

Exam No：9701_s24_qp_43 Year：2024 Question No：9(b)

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33.1.1.1 reaction of an alkylbenzene with hot alkaline KMnO4 and then dilute acid, exemplified by methylbenzene

33.1.2 describe the reaction of carboxylic acids with PCl 3 and heat, PCl 5, or SOCl 2 to form acyl chlorides

33.1.3.1 the oxidation of methanoic acid, HCOOH, with Fehling’s reagent or Tollens’ reagent or acidified KMnO4 or acidified K2Cr2O7 to carbon dioxide and water

33.1.3.2 the oxidation of ethanedioic acid, HOOCCOOH, with warm acidified KMnO4 to carbon dioxide

33.1.4 describe and explain the relative acidities of carboxylic acids, phenols and alcohols

33.1.5 describe and explain the relative acidities of chlorine-substituted carboxylic acids

33.2.1.1 reaction of alcohols with acyl chlorides using the formation of ethyl ethanoate and phenyl benzoate as examples

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