1. (a) Write as many chemically reasonable syntheses as you can think of for ethyl 2-methylpropyl ether (ethyl isobutyl ether). Be sure that at some point in one or more of your syntheses you utilize the following reagents (not all in the same synthesis, however): PBr3, SOCI2, p- toluenesulfonyl chloride (tosyl chloride), NaH, ethanol, 2-methyl-1-propanol (isobutyl alcohol), concentrated H2SO4, Hg(OAc)2, ethene (ethylene).

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1. (a) Write as many chemically reasonable syntheses as you can think of for ethyl 2-methylpropyl ether (ethyl isobutyl ether). Be sure that
at some point in one or more of your syntheses you utilize the following reagents (not all in the same synthesis, however): PB13, SOCI2, p-
toluenesulfonyl chloride (tosyl chloride), NaH, ethanol, 2-methyl-1-propanol (isobutyl alcohol), concentrated H2SO4, Hg(OAc)2, ethene
(ethylene).
(b) Evaluate the relative merits of your syntheses on the basis of selectivity and efficiency. (Decide which ones could be argued to be the
"best" syntheses and which might be "poorer" syntheses.)
Transcribed Image Text:1. (a) Write as many chemically reasonable syntheses as you can think of for ethyl 2-methylpropyl ether (ethyl isobutyl ether). Be sure that at some point in one or more of your syntheses you utilize the following reagents (not all in the same synthesis, however): PB13, SOCI2, p- toluenesulfonyl chloride (tosyl chloride), NaH, ethanol, 2-methyl-1-propanol (isobutyl alcohol), concentrated H2SO4, Hg(OAc)2, ethene (ethylene). (b) Evaluate the relative merits of your syntheses on the basis of selectivity and efficiency. (Decide which ones could be argued to be the "best" syntheses and which might be "poorer" syntheses.)
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