Show how the following ethers might be synthesized using (1) alkoxymercuration– demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)
(e) 1-isopropoxy-1-methylcyclopentane

Both LiAlH₄ and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that become protonated in an aqueous workup). Those alkoxides can react with 1° or methyl alkyl halides or tosylates to give ethers. Show how the following ethers can be formed in this two-step process. As starting materials you may use any reactants containing 7 carbons or fewer.

(a)

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.

(a) cyclopentyl n-propyl ether from cyclopentanol and propan-1-ol

Show how the following ethers might be synthesized using (1) alkoxymercuration– demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)

(d) 1-methoxy-1-methylcyclopentane

Show how the following ethers might be synthesized using (1) alkoxymercuration–demercuration and (2) the Williamson synthesis. (When one of these methods cannot be used for the given ether, point out why it will not work.)

f. tert-butyl phenyl ether

Show how you would synthesize the following ethers in good yield from the indicated starting materials and any additional reagents needed.

(b) n-butyl phenyl ether from phenol and butan-1-ol

Both LiAlH₄ and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that become protonated in an aqueous workup). Those alkoxides can react with 1° or methyl alkyl halides or tosylates to give ethers. Show how the following ethers can be formed in this two-step process. As starting materials you may use any reactants containing 7 carbons or fewer.

(b)

Both LiAlH₄ and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that become protonated in an aqueous workup). Those alkoxides can react with 1° or methyl alkyl halides or tosylates to give ethers. Show how the following ethers can be formed in this two-step process. As starting materials you may use any reactants containing 7 carbons or fewer.

(c)

In Chapter 14, we saw that Agent Orange contains (2,4,5-trichlorophenoxy) acetic acid, called 2,4,5-T. This compound is synthesized by the partial reaction of 1,2,4,5-tetrachlorobenzene with sodium hydroxide, followed by reaction with sodium chloroacetate, ClCH₂CO₂Na.

a. Draw the structures of these compounds, and write equations for these reactions.