Arrange the following reagents in INCREASING order of * nucleophilicity* in protic solvent: NaOCH, NaSCH, CH;OH CH,SH CH;CO,H Next arrange them in increasing order of nucleophilicity in aprotic solvent. Next arrange them in increasing order of basicity. Explain any differences between the different orderings.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.SE: Something Extra
Problem 37AP
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Arrange the following reagents in INCREASING order of * nucleophilicity* in protic solvent:
NaOCH,
NaSCH,
CH;OH
CH,SH
CH;CO,H
Next arrange them in increasing order of nucleophilicity in aprotic solvent. Next arrange them
in increasing order of basicity. Explain any differences between the different orderings.
Transcribed Image Text:Arrange the following reagents in INCREASING order of * nucleophilicity* in protic solvent: NaOCH, NaSCH, CH;OH CH,SH CH;CO,H Next arrange them in increasing order of nucleophilicity in aprotic solvent. Next arrange them in increasing order of basicity. Explain any differences between the different orderings.
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