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

Verified step by step guidance

1. Step 1: Begin with the starting material, 2-methylcyclohexanol. Recognize that the hydroxyl group (-OH) on the cyclohexanol must be converted into a good leaving group to facilitate the ether synthesis.
2. Step 2: Convert the hydroxyl group into a better leaving group by reacting 2-methylcyclohexanol with a reagent like p-toluenesulfonyl chloride (TsCl) in the presence of a base such as pyridine. This will form the tosylate derivative, 2-methylcyclohexyl tosylate.
3. Step 3: Prepare the ethoxide nucleophile by reacting ethanol (C₂H₅OH) with a strong base such as sodium hydride (NaH) or sodium metal (Na). This generates sodium ethoxide (C₂H₅O⁻), a strong nucleophile.
4. Step 4: Perform an S_N2 reaction by reacting the 2-methylcyclohexyl tosylate with sodium ethoxide. The ethoxide ion will attack the carbon bonded to the tosylate group, displacing the tosylate and forming 1-ethoxy-1-methylcyclohexane.
5. Step 5: Purify the product using standard organic chemistry techniques such as distillation or chromatography to isolate 1-ethoxy-1-methylcyclohexane in good yield.

Key Concepts

Ethers and Their Synthesis

Ethers are organic compounds characterized by an oxygen atom bonded to two alkyl or aryl groups. They can be synthesized through various methods, including the Williamson ether synthesis, which involves the reaction of an alkoxide ion with a primary alkyl halide. Understanding the reactivity and properties of ethers is crucial for designing effective synthetic routes.

Alcohols as Reactants

Alcohols, such as 2-methylcyclohexanol, serve as important starting materials in organic synthesis. They can undergo various transformations, including dehydration to form alkenes or nucleophilic substitution to produce ethers. Recognizing the functional groups and their reactivity patterns is essential for planning the synthesis of target compounds.

Nucleophilic Substitution Reactions

Nucleophilic substitution reactions, particularly SN2 mechanisms, are fundamental in organic chemistry for forming new bonds. In the context of ether synthesis, a nucleophile (like an alkoxide) attacks an electrophilic carbon in an alkyl halide, leading to the formation of the ether. Understanding the conditions that favor SN2 reactions, such as sterics and solvent effects, is vital for achieving good yields.