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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

Which of the following is produced when anisole reacts with HI?

A

Benzaldehyde and ethanol

B

Acetophenone

C

Iodobenzene and methanol

D

Phenol and methyl iodide

Step-by-Step Solution

  1. Reactants: Anisole is methyl phenyl ether (C6H5−O−CH3C_6H_5-O-CH_3). HI is Hydrogen Iodide.
  2. Mechanism: The reaction involves the cleavage of the ether linkage. In alkyl aryl ethers, the oxygen atom is attached to a benzene ring. The lone pair on the oxygen enters into resonance with the benzene ring, imparting a partial double bond character to the Cphenyl−OC_{phenyl}-O bond. This makes the Cphenyl−OC_{phenyl}-O bond much stronger and difficult to break compared to the Cmethyl−OC_{methyl}-O bond.
  3. Cleavage: Consequently, the weaker O−CH3O-CH_3 bond breaks. The proton (H+H^+) from HI protonates the oxygen.
  4. Nucleophilic Attack: The iodide ion (I−I^-) attacks the smaller alkyl group (methyl group) via an SN2S_N2 mechanism.
  5. Products: This results in the formation of Phenol (C6H5OHC_6H_5OH) and Methyl Iodide (CH3ICH_3I).
  6. Conclusion: The products are Phenol and methyl iodide.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAlcohols, Phenols and Ethersfollowingproducedanisolereacts

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When phenol is treated with CHCl₃ and NaOH, the product formed is:

A.Benzaldehyde
B.Salicylaldehyde
C.Salicylic acid
D.Benzoic acid
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Which of the following statement is correct for the stability of ions of ethyl alcohol and phenol:

A.Delocalization of π-electrons in phenoxide ion
B.Delocalization of electrons in ethoxide ion
C.Inductive effect of ethyl and phenyl group
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When glycerol is treated with an excess of HI, it produces:

A.Allyl iodide
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A.Chlorobenzene
B.Bromobenzene
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A.Option 1
B.Option 2
C.Option 3
D.Option 4
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A.Toluene
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A.Option 1
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C.4
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C.b > a > c > d
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