CH 3 OC 2 H 5 And ( CH 3)3 C - OCH 3 Are Treated With Hydroiodic ...

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4. CH 3 OC 2 H 5 and ( CH 3)3 C - OCH 3 are treated with hydroiodic acid. The fragments after reactions obtained are

Q. CH3​OC2​H5​ and (CH3​)3​C−OCH3​ are treated with hydroiodic acid. The fragments after reactions obtained are 2169 157 AIIMSAIIMS 2007Alcohols Phenols and Ethers Report Error A

CH3​I+HOC2​H5​;(CH3​)3​C−1+HOCH3​

26% B

CH3​OH+C2​H5​I;(CH3​)3​Cl+HOCH3​

25% C

CH3​OH+C2​H5​;(CH3​)3​C−OH+CH3​I

27% D

CH3​I+HOC2​H5​;CH3​I+(CH3​)3​−C−OH

21%

Solution:

When mixed ethers are used, the alkyl iodide produced depends on the nature of alkyl groups. If one group is Me and the other a pri-or sec-alkyl group, then methyl iodide is produced. Here reaction occurs via SN​2 mechanism and because of the steric effect of the larger group, I− attacks the smaller (Me) group. CH3​OC2​H5​+HI→CH3​I+C2​H5​OH When the substrate is a methyl t -alkyl ether, the products are t−RI and MeOH. Here reaction occurs by SN​! mechanism and formation of products is controlled by the stability of carbocation. Since carbocation stability order is 3∘>2∘>1∘>CH3​⊕​ ∴ Alkyl halide is always derived from tert-alkyl group.