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Alcohols Phenols and Ethers question

2021 · 22 Jul · Shift 2 · Q12
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Alcohols Phenols and Ethers question

2021 · 22 Jul · Shift 2 · Q12

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
An organic compound A (C6H6OC_6H_6OC6​H6​O) gives dark green colouration with ferric chloride. On treatment with CHCl3CHCl_3CHCl3​ and KOHKOHKOH, followed by acidification gives compound B. Compound B can also be obtained from compound C on reaction with pyridinium chlorochromate (PCC). Identify A, B and C.
  1. A
    JEE Main 2021 (Online) 22th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 100 English Option 1
  2. B
    JEE Main 2021 (Online) 22th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 100 English Option 2
  3. C
    JEE Main 2021 (Online) 22th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 100 English Option 3
  4. D
    JEE Main 2021 (Online) 22th July Evening Shift Chemistry - Alcohols, Phenols and Ethers Question 100 English Option 4
View written solutionFree

Correct answer: A

  1. Identify compound A from molecular formula and test

    The compound has formula C6H6OC_6H_6OC6​H6​O and gives a dark green colour with ferric chloride.

    • Ferric chloride test indicates the presence of a phenolic −OH-OH−OH group.
    • The compound with formula C6H6OC_6H_6OC6​H6​O containing a phenolic group is phenol: C6H5OHC_6H_5OHC6​H5​OH

    So, A = phenol.

  2. Reaction of phenol with CHCl3/KOHCHCl_3/KOHCHCl3​/KOH followed by acidification

    This is the Reimer–Tiemann reaction.

    Phenol on treatment with CHCl3CHCl_3CHCl3​ and KOHKOHKOH, followed by acidification, gives mainly o-hydroxybenzaldehyde (salicylaldehyde).

    C6H5OH→acidificationCHCl3/KOHo-HOC6H4CHOC_6H_5OH \xrightarrow[\text{acidification}]{CHCl_3/KOH} o\text{-}HOC_6H_4CHOC6​H5​OHCHCl3​/KOHacidification​o-HOC6​H4​CHO

    So, B = salicylaldehyde (2-hydroxybenzaldehyde).

  3. Identify compound C such that PCC gives B

    PCC oxidizes a primary alcohol to an aldehyde without further oxidation to acid.

    Since B is ooo-hydroxybenzaldehyde, the corresponding alcohol C must be:

    o-HOC6H4CH2OHo\text{-}HOC_6H_4CH_2OHo-HOC6​H4​CH2​OH

    which is 2-hydroxybenzyl alcohol (salicyl alcohol).

    o-HOC6H4CH2OH→PCCo-HOC6H4CHOo\text{-}HOC_6H_4CH_2OH \xrightarrow{PCC} o\text{-}HOC_6H_4CHOo-HOC6​H4​CH2​OHPCC​o-HOC6​H4​CHO

    So, C = 2-hydroxybenzyl alcohol.

  4. Final identification

    • A=A =A= Phenol
    • B=B =B= o-Hydroxybenzaldehyde (salicylaldehyde)
    • C=C =C= o-Hydroxybenzyl alcohol
  5. Match with options

    This set corresponds to Option A.

Therefore, the correct answer is A.

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