Write the products of the following reaction :
\[
(CH_3)_3C-O-C_2H_5
\xrightarrow{HI}
?
\]
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Solution and Explanation
When an ether has one tertiary alkyl group and one primary group, HI cleaves at the tertiary C-O bond via $S_N1$, because a tertiary carbocation is far more stable than a primary one.
Step 2: Protonation and bond cleavage.
$H^+$ from HI protonates the ether oxygen, then the C-O bond at the tertiary side breaks: $(CH_3)_3C-O-C_2H_5 + H^+ \rightarrow (CH_3)_3C^+ + C_2H_5OH$.
Step 3: Iodide attacks the carbocation.
$I^-$ combines with $(CH_3)_3C^+$ to give tert-butyl iodide; the two products are:
\[ \boxed{(CH_3)_3CI + C_2H_5OH} \]
Top Questions on Ethers
IUPAC name of the given ether is:
- MHT CET - 2024
- Chemistry
- Ethers
Replacement of a hydrogen atom in a hydrocarbon by an alkoxy or carboxyl group yields a class of compounds known as ethers. Ethers are classified as symmetrical or unsymmetrical on the basis of groups attached to the oxygen atoms. Diethyl ether, a symmetrical ether, has been widely used as an inhalation anesthetic. Ethers can be prepared by acid catalyzed intermolecular dehydration of alcohols and Williamson's synthesis. Acid catalyzed dehydration of alcohols is not generally preferred as it gives a mixture of elimination and substitution products. In Williamson's synthesis, an alkyl halide is allowed to react with sodium alkoxide. Ethers containing substituted Alkyl groups may also be prepared by this method. The C-O bond in ether is weakly polar and is cleaved under drastic conditions with excess of hydrogen halides. In electrophilic substitution, the alkoxy group deactivates the aromatic ring and directs the incoming group to ortho and para positions.
- Which of the following reagents is required for the conversion of Benzene to methyl benzoate?
(A) Br\(_2\)/FeBr\(_3\)
(B) Mg, dry Ether
(C) CO\(_2\), H\(_3\)O\(^+\)
(D) Methanol, Conc. H\(_2\)SO\(_4\) - What happens when C₆H₅–O–R is treated with HX?
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