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Aldehydes Ketones and Carboxylic Acids question

2014 · Shift 0 · Q10
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Aldehydes Ketones and Carboxylic Acids question

2014 · Shift 0 · Q10

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
Sodium phenoxide when heated with CO2C{O_2}CO2​ under pressure at 125∘C{125^ \circ }C125∘C yields a product which on acetylation products C.C.C.JEE Main 2014 (Offline) Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 227 English The major product CCC would be
  1. A
    JEE Main 2014 (Offline) Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 227 English Option 1
  2. B
    JEE Main 2014 (Offline) Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 227 English Option 2
  3. C
    JEE Main 2014 (Offline) Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 227 English Option 3
  4. D
    JEE Main 2014 (Offline) Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 227 English Option 4
View written solutionFree

Correct answer: A

  1. Identify the reaction of sodium phenoxide with CO2CO_2CO2​ under pressure

    Sodium phenoxide reacts with carbon dioxide under pressure at about 125∘C125^\circ C125∘C via the Kolbe–Schmitt reaction.

    \ceC6H5ONa+CO2−>[125∘C, pressure]o−HOC6H4COONa\ce{C6H5ONa + CO2 ->[125^\circ C,\ pressure] o-HOC6H4COONa}\ceC6H5ONa+CO2−>[125∘C, pressure]o−HOC6H4COONa

    On acidification, this gives salicylic acid (ooo-hydroxybenzoic acid):

    \ceo−HOC6H4COONa−>[H+]o−HOC6H4COOH\ce{o-HOC6H4COONa ->[H^+] o-HOC6H4COOH}\ceo−HOC6H4COONa−>[H+]o−HOC6H4COOH

  2. Now consider acetylation of salicylic acid

    Salicylic acid contains:

    • one phenolic −OH-OH−OH
    • one carboxylic acid −COOH-COOH−COOH

    Under acetylation, the phenolic −OH-OH−OH is acetylated preferentially, forming acetylsalicylic acid (aspirin), i.e. ooo-acetoxybenzoic acid.

    \ceo−HOC6H4COOH+CH3COCl (or) (CH3CO)2O−>o−CH3COOC6H4COOH\ce{o-HOC6H4COOH + CH3COCl\ (or)\ (CH3CO)2O -> o-CH3COOC6H4COOH}\ceo−HOC6H4COOH+CH3COCl (or) (CH3CO)2O−>o−CH3COOC6H4COOH

  3. Thus the major product CCC is:

    2-acetoxybenzoic acid (acetylsalicylic acid, aspirin)\text{2-acetoxybenzoic acid (acetylsalicylic acid, aspirin)}2-acetoxybenzoic acid (acetylsalicylic acid, aspirin)

  4. Match with options

    The stored correct answer is A, so option A must correspond to acetylsalicylic acid.

Therefore, the major product is Option A.

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