Question

Find the product for

CH₃CH₂ - O - CH₂ - CH₂ - O - CH₂ - C₆H₅ + HI(excess)

(a) HO-CH₂CH₂-OH, C₆H₅CH₂ - I, CH₃CH₂ - I

(b) C₆H₅CH₂-OH, CH₃CH₂ - I, I-CH₂CH₂ - OH

(c) I - CH₂CH₂ - I, C₆H₅CH₂ - I, CH₃CH₂ - OH

(d) HO-CH₂CH₂ - OH, C₆H₅CH₂ - I, CH₃CH₂ - OH

Answer 1

The correct option is: (a) HO-CH₂CH₂-OH, C₆H₅CH₂ - I, CH₃CH₂ - I

Explanation:

Presence of excess of HI favours S_N1 mechanism. 

So, formation of products is controlled by the stability of the carbocation resulting in the cleavage of C - O bond in protonated ether. Thus the product for given equation are C₆H₅CH₂I, CH₃CH₂I, HOCH₂ - CH₂OH.