Question:
$tert-butyl\, methyl$ ether on treatment with hydrogen iodide in cold gives
$tert-butyl\, methyl$ ether on treatment with hydrogen iodide in cold gives
Updated On: Jul 13, 2024
- tert-butyl iodide and methyl iodide
- tert-butyl alcohol and methyl alcohol
- tert-butyl alcohol and methyl iodide
- tert-butyl iodide and methyl alcohol
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The Correct Option is D
Solution and Explanation
Tert-butyl methyl ether on treatment with hydrogen iodide in cold gives tert-butyl iodide and methyl alcohol.
$\left( CH _{3}\right)_{3} C - O - CH _{3}+ HI \ce{->[\text { cold }]}\left( CH _{3}\right)_{3} C - I + CH _{3}- OH$ When one of the alkyl groups is tertiary, then tertiary alkyl halide an lower alcohol is formed. (proceeds through the $SN ^{1}$ mechanism since tertiary carbocation is most stable)
$\left( CH _{3}\right)_{3} C - O - CH _{3}+ HI \ce{->[\text { cold }]}\left( CH _{3}\right)_{3} C - I + CH _{3}- OH$ When one of the alkyl groups is tertiary, then tertiary alkyl halide an lower alcohol is formed. (proceeds through the $SN ^{1}$ mechanism since tertiary carbocation is most stable)
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Concepts Used:
Ethers
A class of organic compounds that mostly contain an ether group in which the oxygen atom is bonded to two alkyl or aryl groups are referred to as Ethers. For the same, C-O-C is the functional group.
Chemical Properties of Ether:
Ethers are less polar as well as less reactive, and they do not react with active metals (Na, K), cold dilute acid, oxidizing and reducing agents or other chemicals.
The reason is that they do not have an active functional group.
- Because of the presence of a lone pair on the oxygen atom, ether has a basic nature and behaves like a Lewis base. Formation of oxonium ion occurs when ethers react with cold conc. acid. Ethers, such as BF3, AICI3, and RMgX, form a dative bond with Lewis acid.
- There is a significant difference between the boiling points of ethanol and dimethyl ether. Ethanol has very much higher boiling point of 78 degrees Celsius, whereas dimethyl ether has a negative 25 degrees boiling point. And this explains the molecules' state of matter.
- Ethanol is, of course, a liquid at room temperature and pressure because its boiling point is higher than room temperature. On the other hand, Dimethyl ether already has turned into a gas due to its much lower boiling point.