Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Alcohols Phenols and Ethers question

2018 · Shift 0 · Q7
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Main
  3. /Chemistry
  4. /Alcohols Phenols and Ethers
  5. /2018 · Shift 0 · Q7

Alcohols Phenols and Ethers question

2018 · Shift 0 · Q7

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Phenol on treatment with CO2CO_2CO2​ in the presence of NaOHNaOHNaOH followed by acidification produces compound X as the major product. X on treatment with (CH3CO)2O(CH_3CO)_2O(CH3​CO)2​O in the presence of catalytic amount of H2SO4H_2SO_4H2​SO4​ produces:
  1. A
    JEE Main 2018 (Offline) Chemistry - Alcohols, Phenols and Ethers Question 155 English Option 1
  2. B
    JEE Main 2018 (Offline) Chemistry - Alcohols, Phenols and Ethers Question 155 English Option 2
  3. C
    JEE Main 2018 (Offline) Chemistry - Alcohols, Phenols and Ethers Question 155 English Option 3
  4. D
    JEE Main 2018 (Offline) Chemistry - Alcohols, Phenols and Ethers Question 155 English Option 4
View written solutionFree

Correct answer: B

  1. Identify compound X

Phenol treated with NaOHNaOHNaOH forms sodium phenoxide, which on reaction with CO2CO_2CO2​ followed by acidification undergoes the Kolbe–Schmitt reaction.

The major product is salicylic acid (ooo-hydroxybenzoic acid).

Phenol→NaOHsodium phenoxide→CO2→H+o-hydroxybenzoic acid\text{Phenol} \xrightarrow{NaOH} \text{sodium phenoxide} \xrightarrow{CO_2} \xrightarrow{H^+} o\text{-hydroxybenzoic acid}PhenolNaOH​sodium phenoxideCO2​​H+​o-hydroxybenzoic acid

So,

X=o-hydroxybenzoic acid (salicylic acid)X = o\text{-hydroxybenzoic acid (salicylic acid)}X=o-hydroxybenzoic acid (salicylic acid)
  1. Reaction of X with acetic anhydride

Salicylic acid contains:

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

On treatment with acetic anhydride, (CH3CO)2O(CH_3CO)_2O(CH3​CO)2​O, in presence of catalytic H2SO4H_2SO_4H2​SO4​, the phenolic −OH-OH−OH gets acetylated to form an ester.

Thus salicylic acid gives acetylsalicylic acid (aspirin), i.e. 2-acetoxybenzoic acid.

Reaction:

HO–C6H4–COOH+(CH3CO)2O→CH3COO–C6H4–COOH+CH3COOH\text{HO–C}_6\text{H}_4\text{–COOH} + (CH_3CO)_2O \rightarrow CH_3COO–C_6H_4–COOH + CH_3COOHHO–C6​H4​–COOH+(CH3​CO)2​O→CH3​COO–C6​H4​–COOH+CH3​COOH
  1. Product formed

The product is:

  • o-acetoxybenzoic acid
  • also called acetylsalicylic acid (aspirin)
  1. Matching with options

Since the stored correct answer is B, the option corresponding to acetylsalicylic acid (aspirin) must be B.

Therefore, the correct answer is:

B\boxed{B}B​
PreviousNext

More from Alcohols Phenols and Ethers

  • The major product of the following reaction is : Includes diagram2017 · MCQ
  • The increasing order of the boiling points for the following compounds is : Includes diagram2017 · MCQ
  • Bouveault-Blanc reduction reaction involves :2016 · MCQ
  • The gas evolved on heating CH3​MgBr in methanol is :2016 · MCQ
  • The product of the reaction given below is : Includes diagram2016 · MCQ
  • 2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields: Includes diagram2016 · MCQ
  • The most suitable reagent for the conversion of R - CH2​ - OH → R - CHO is:2014 · MCQ
  • An unknown alcohol is treated with the “Lucas reagent” to determine whether the alcohol is primary, secondary or tertiary. Which alcohol reacts fastest and by what mechanism:2013 · MCQ