TBR OChem S8 Q84

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ajumobim

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(NO2)2C6H3COCl is NOT a good reactant to test for which of the following?
A) Alcohol (ROH)
B) Amine (RNH2)
C) Ether (ROR)
D) Thiol (RSH)
C is the correct answer.

Nucleophile strength is directly proportional to base strength (capability of donating electron pairs) so why are ethers not as nucleophilic as alcohols, amines, and thiols since the oxygen carries lone pairs like the others?

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Definitely keep in mind is that ethers are generally unreactive (especially when compared to the other choices in this questions), which is one of the reasons they're used as solvents in a handful of chemical reactions.
 
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