1. Which is a stronger base ethanol (CH3CH2OH) or ethoxide anion (CH3CH2O-ve) and why. 2. Rank...
1. Which is a stronger base ethanol (CH3CH2OH) or ethoxide anion (CH3CH2O-ve) and why.
2. Rank the following bases from strongest to weakest and explain why you put the bases in that order. a) diisopropyl amide b) ethanethiolate c) ethoxide anion d) tert-butoxide anion
Homework Answers
1) Ethoxide anion is stronger base because presence of negative charge increase the electron density and thus basicity.
2) Order is :
(Strongest) (weakest)
a) > b) > c) > d)
Since lone pair on nitrogen in diisopropylamide is in resonance thus it is less available for donation and it is least basic. Oxygen in ethoxide ion is more basic than Sulphur in ethanethiolate because electron density on oxygen is more than that of sulphur. tert-butoxide is more basic because +I effect of tert butyl group is higher than ethane hence electron density on tert-butoxide is high. Thus, tert-butoxide is more basic.
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