Consider the following reaction. [figure] In the light of the above statements, choose the correct answer from the options given below :
- Both Statement I and Statement II are true
- Both Statement I and Statement II are false
- Statement I is true but Statement II is false
- Statement I is false but Statement II is true
Answer
(4) Statement I is false but Statement II is true
Solution
C6H5-O-CH2-C6H5 + HI C6H5- OH-CH2C6H5 + I
The O-C6H5 (aryl) bond has partial double-bond character due to resonance and cannot be attacked, so it is not cleaved.
I attacks the benzylic CH2 carbon (stable benzylic carbocation / easy SN) ⇒ the -O-CH2- bond breaks:
C6H5OCH2C6H5 + HI C6H5OH + C6H5CH2I
Products: phenol and benzyl iodide (not benzyl alcohol and iodobenzene) ⇒ Statement I is false.
The -O-CH2- bond is cleaved ⇒ Statement II is true.
Answer: (4)