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Bases that can deprotonate a terminal alkyne

A. Sodium amide (NaNH2)
B. Potassium hydroxide (KOH)
C. Lithium diisopropylamide (LDA)
D. Sodium hydride (NaH)

1 Answer

4 votes

Final answer:

Sodium amide (NaNH2), lithium diisopropylamide (LDA), and sodium hydride (NaH) are strong bases that can deprotonate a terminal alkyne. Potassium hydroxide (KOH) cannot deprotonate a terminal alkyne.

Step-by-step explanation:

Terminal alkynes have acidic protons but they are weak acids (pKa ~25). In order to deprotonate a terminal alkyne, you would need a strong base. Sodium amide (NaNH2), lithium diisopropylamide (LDA), and sodium hydride (NaH) are all strong bases that can deprotonate a terminal alkyne. Potassium hydroxide (KOH) is not a strong enough base to remove all of the alkyne protons.

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