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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.

Short Answer

Expert verified

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

Step by step solution

01

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

02

 Preparation of Cyclohexyl methyl ether

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

  • cyclohexanolate reacted with Iodomethane(SN2reaction) forms the desired product methylcyclohexane, and this is an excellent method of preparing desired ether as Iodomethane is very much reactive inSN2 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

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Most popular questions from this chapter

Treatment of 1-bromo-2-deuterio-2-phenylethane with strong base leads to a mixture of deuterated and nondeuterated phenylethylenes in an approximately 7;1 ratio. Explain

Which compound in each of the following pairs will react faster in an SN2reaction with OH-?

(b) CH3CH2Iin ethanol or dimethyl sulfoxide

Which reactant in each of the following pairs is more nucleophilic? Explain.

(e) I- or Cl-

Question: (R)-2-Bromooctane undergoes racemization to give (卤)-2-bromooctane when treated with NaBr in dimethyl sulfoxide. Explain.

Tell whether each of the following reactions is likely to be SN1, SN2, E1, E1cB or E2:

b)

See all solutions

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