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Diethyl ether (CH3CH2-O-CH2CH3) does NOT react with which of the following reagents?

1. Na
2. NaNH2
3. Aqueous HCl
4. Aqueous NaOH

Correct answer: Aqueous NaOH

Solution

Diethyl ether does not react with Na (no acidic H), does not react with NaNH2 (not sufficiently acidic), does react with concentrated HCl (protonation of O then nucleophilic substitution), and does NOT react with aqueous NaOH (ethers are resistant to dilute base). The reagent it does not react with is aqueous NaOH.

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