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In which of the following reactions are incorrect products shown? (A) (CH3)3C-O-CH3 + HI -> (CH3)3C-OH + CH3I (B) CH3-O-CH2-CH3 + HI -> CH3OH + ICH2CH3 (C) C6H5-O-CH2-C6H5 + HI -> C6H5-I + C6H5-CH2-OH (D) Anisole (C6H5-O-CH3) + HI -> C6H5-OH + CH3I

1. (A) (CH3)3C-O-CH3 + HI gives (CH3)3C-OH + CH3I
2. (B) CH3-O-CH2-CH3 + HI gives CH3OH + ICH2CH3
3. (C) C6H5-O-CH2-C6H5 + HI gives C6H5-I + C6H5-CH2-OH
4. (D) Anisole + HI gives phenol + CH3I

Correct answer: (C) C6H5-O-CH2-C6H5 + HI gives C6H5-I + C6H5-CH2-OH

Solution

In the cleavage of C6H5-O-CH2-C6H5 with HI, the iodide attacks the benzylic carbon (benzyl is more reactive and sp3). The correct products are phenol (C6H5-OH) and benzyl iodide (C6H5-CH2-I). Option C incorrectly shows C6H5-I (phenyl iodide) as a product, which cannot form since the aryl C-O bond is not cleaved by HI under normal conditions.

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