Select the ether among following that yields methanol as one of the products on reaction with cold hydroiodic acid

Question

Select the ether among following that yields methanol as one of the products on reaction with cold hydroiodic acid (A) 1-Methoxybutane (B) 1-Methoxy-2-methylpropane (C) 2-Methoxy-2-methylpropane (D) Methoxybenzene

Tardigrade Admin · Accepted Answer

According Zeisel method, when an ether reacts with cold

H I

, alkyl iodide and alcohol are formed. In case of asymmetrical ether, the alkyl halide is always formed from the smaller alkyl group provided no tertiary

(3^{\circ})

alkyl group is present and if any

3^{\circ}

alkyl group is present, the halogen gets attached with it. In case of alkyl aryl ethers, the products are always phenol and an alkyl halide.

(a)

C H_{3} - O - C_{4} H_{9} + H I ⟶ Cold C H_{3} I + C_{4} H_{9} O H

(b)

C H_{3} — O — C H_{2} — C ∣ H_{3} C H — C H_{3} + H I ⟶ Cold

C H_{3} I + C H_{3} — C ∣ H_{3} C H — C H_{3} — O H

Q. Select the ether among following that yields methanol as one of the products on reaction with cold hydroiodic acid

$1$ -Methoxybutane

$1$ -Methoxy- $2$ -methylpropane

$2$ -Methoxy- $2$ -methylpropane

Methoxybenzene