Q60E Ethers can often be prepared by ... [FREE SOLUTION]

Chapter 11: Q60E (page 350)

Ethers can often be prepared by SN2 reaction of alkoxide ions, ${RO}^{-}$ ,with alkyl halides. Suppose you wanted to prepare cyclohexyl methylether. Which of the two possible routes shown below would youchoose? Explain.

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Bimolecular Nucleophilic substitution chemical reaction (SN2)

In a Bimolecular Nucleophilic substitution chemical reaction,substituting an optically active compound with the nucleophile through a backside attack forms the product of inversion stereochemistry.

This reaction occurs in a polar aprotic solvent, e.g., acetone

Preparation of Cyclohexyl methyl ether

Cyclohexyl methyl ether is formed by two methods shown as follows:

cyclohexanolate reacted with Iodomethane $(S_{N} 2reaction)$ forms the desired product methylcyclohexane, and this is an excellent method of preparing desired ether as Iodomethane is very much reactive in $S_{N} 2$ displacement reaction.

An excellent method for the formation of methoxyhexane

Iodocyclohexane is a secondary haloalkane that reacts with base methoxide ion, forms the substituted product methoxyhexane, and the elimination product cyclohexene. This method forms other side products and the desired product; thus is a less satisfactory method for preparing ether

Less satisfactory method for the formation of methoxyhexane