Textbook Question
Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.
(e) 1-ethoxy-1-methylcyclohexane from 2-methylcyclohexanol
12. Alcohols, Ethers, Epoxides and Thiols
Making Ethers - Cumulative Practice
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Predict the product of the following reaction.
A
B
C
D
Verified step by step guidance1
Identify the starting material as an alkene, specifically 2-methyl-2-butene.
Recognize the reaction conditions: acidic medium (H+) and ethanol (EtOH), which suggests an acid-catalyzed hydration or ether formation.
Understand that the first step involves protonation of the alkene to form a more stable carbocation. The proton (H+) will add to the less substituted carbon of the double bond, forming a tertiary carbocation at the more substituted carbon.
Consider the nucleophilic attack by ethanol (EtOH) on the carbocation. The oxygen in ethanol will donate a pair of electrons to the carbocation, forming an ethyl ether linkage.
Finally, deprotonation of the oxonium ion (formed after the nucleophilic attack) by a base (often the solvent or another ethanol molecule) will yield the final ether product, 2-ethoxy-2-methylbutane.
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