Question

In the reaction
`(CH_(3))_(3)C-O-CH_(2)CH_(3)+underset((1"mole"))(HI)overset(heat)(rarr)` the products formed is (are)
A. `(CH_(3))_(3)COH and CH_(3)CH_(2)l`
B. `(CH_(3))_(3)Cl and CH_(3)CH_(2)I`
C. `(CH_(3))_(3)CI and CH_(3)CH_(2)OH`
D. `(CH_(3))_(3)C-underset(H)underset(|)overset(+)(O)-CH_(2)CH_(2)CH_(3)I^(-)`

Answer 1

Correct Answer - D
When the substrate is an ethyl `t-`alkyl ether, the products are `t-RI` and `EtOH`. This can be esplained by an `S_(N)1` mechanism, the carbocation produced being the tertiary carbocation since this type is more stable than a primary or secondary carbocation.
`(CH_(3))_(3)C-O-CH_(2)CH_(3)overset(HI)(rarr)(CH_(3))_(3)Cl+CH_(3)CH_(2)OH`