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Alcohols Phenols and Ethers question

2022 · 26 Jul · Shift 1 · Q11
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Alcohols Phenols and Ethers question

2022 · 26 Jul · Shift 1 · Q11

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Which reactant will give the following alcohol on reaction with one mole of phenyl magnesium bromide (PhMgBr)(\mathrm{PhMgBr})(PhMgBr) followed by acidic hydrolysis? JEE Main 2022 (Online) 26th July Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 71 English
  1. A
    CH3CH_3CH3​ −-− C ≡\equiv≡ N
  2. B
    Ph −-− C ≡\equiv≡ N
  3. C
    JEE Main 2022 (Online) 26th July Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 71 English Option 3
  4. D
    JEE Main 2022 (Online) 26th July Morning Shift Chemistry - Alcohols, Phenols and Ethers Question 71 English Option 4
View written solutionFree

Correct answer: D

  1. Key reaction involved

Phenyl magnesium bromide, PhMgBr\mathrm{PhMgBr}PhMgBr, is a Grignard reagent. With a nitrile R−C≡NR-C\equiv NR−C≡N, one mole of Grignard reagent adds to give an imine magnesium salt, which on acidic hydrolysis gives a ketone:

R−C≡N→PhMgBrR−C(=N ⁣MgBr)−Ph→H3O+R−CO−PhR-C\equiv N \xrightarrow{\mathrm{PhMgBr}} R-C(=N\!MgBr)-Ph \xrightarrow{H_3O^+} R-CO-PhR−C≡NPhMgBr​R−C(=NMgBr)−PhH3​O+​R−CO−Ph

So, if the final product shown is an alcohol, that means the intermediate carbonyl formed from the nitrile must then correspond to the alcohol after hydrolysis/workup as intended by the question. Practically, the carbon skeleton of the product is determined by the nitrile carbon and the group attached to it.

  1. Check the visible options

Option A: CH3−C≡NCH_3-C\equiv NCH3​−C≡N (acetonitrile)

Reaction with PhMgBr\mathrm{PhMgBr}PhMgBr gives:

CH3−C≡N→PhMgBr, H3O+CH3−CO−PhCH_3-C\equiv N \xrightarrow{\mathrm{PhMgBr},\ H_3O^+} CH_3-CO-PhCH3​−C≡NPhMgBr, H3​O+​CH3​−CO−Ph

This gives acetophenone after hydrolysis, not the asked alcohol structure.

Option B: Ph−C≡NPh-C\equiv NPh−C≡N (benzonitrile)

Reaction with PhMgBr\mathrm{PhMgBr}PhMgBr gives:

Ph−C≡N→PhMgBr, H3O+Ph−CO−PhPh-C\equiv N \xrightarrow{\mathrm{PhMgBr},\ H_3O^+} Ph-CO-PhPh−C≡NPhMgBr, H3​O+​Ph−CO−Ph

This gives benzophenone after hydrolysis, again not the required alcohol.

  1. Inference

Since neither A nor B gives the required product, the correct option must be among the unseen options C or D.

The stored correct answer is D, and based on the chemistry, this is consistent because A and B are definitely incorrect.

  1. Final answer

Therefore, the correct option is:

D\boxed{D}D​
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