Question

How would you prepare the following ethers?

Short answer

(a)

(b)

(c)

(d)

(e)

(f)

Step-by-step solution

Step-by-Step Solutions Step 1: Alkoxymercuration-Demurcuration reaction

During an alkoxymercuration reaction, the reaction of an alkene with suitable mercury salt and an alcohol occurs. The reagent used in the reaction is NaBH₄(sodium borohydride) which will undergo a reductive demercuration and yield corresponding ethers.

Alkoxymercurationreaction occurs when an alkene is treated with an alcoholin the presence of mercuric acetate or, even better, mercuric trifluoroacetate (CF₃CO₂)₂Hg. Demercuration by reaction with NaBH₄ then yields an ether. The net result isMarkovnikov addition of the alcohol to the alkene.

The Williamson Ether Synthesis

Williamson Ether Synthesis is the reaction that uses deprotonated alcohol and an organohalide to form an ether.The most generally useful method of preparing ethers involves Williamson ether synthesis,in which an alkoxide ion reacts with a primary alkyl halide or tosylate in an S_N2 reaction. The structure of ethers was proved due to this chemical reaction.

Prepare the following given ethers

(a) The given compound (a) can be synthesized from the Williamson synthesis as shown below:

Preparation of compound (a)

(b)The given compound (b) can be synthesized from an alkoxymercuration reaction as shown below:

Preparation of compound (b)

(c) The given compound (c) can be synthesized by treating but-2-ene with meta- Chloroprepoxybenzoic RCO₃H as shown below:

Preparation of compound (c)

[RCO₃H = meta-Chloroprepoxybenzoic acid]

(d)The given compound (d) can be synthesized from an alkoxymercuration reaction as shown below:

Preparation of compound (d)

(e)The given compound (e) can be synthesized by treating cyclohexene withmeta-Chloroprepoxybenzoic RCO₃H and then further undergo Williamson synthesis to get the desired product as shown below:

Preparation of compound (e)

(f)The given compound (f) can be synthesized by Hydroboration of cyclohexene and then undergo Williamson synthesis to get the desired product as shown below:

Preparation of compound (f)