Match the starting material in Column I with the products formed (Column II) in the reaction with HI.

Column I

Column II

A. 1.
B. 2.
C. 3.
D. 4.
5.
 
A B C D
1. 2 3 4 1
2. 3 1 5 2
3. 5 4 3 2
4. 4 5 2 1
Hint: Cleavage of C–O bond in ethers

i. Reactant A  is a symmetrical ether so the products are methanol and methyl iodide. The reaction is as follows:

B. In the case of unsymmetrical ether, one alkyl group is primary while another is secondary. So, it follows SN2 mechanism. Thus, the halide ion attacks the smaller alkyl group, and the products are as follows:

C. In the third example, one of the alkyl group is tertiary and the other is primary. It follows SN1 mechanism and halide ion attacks the tertiary alkyl group and the products are as follows:

D. In the case of alkyl aryl ether. In this ether, the bond is weaker than the bond which has a partial double bond character due to resonance. So, the halide ion attacks on the alkyl group and the products are as follows: