Problem: The pKa of CH3NH2 is 40, while the pKa of HCN is 9.(a) Explain this difference in acidity.(b) Can the cyanide anion (the conjugate base of HCN) be used as a base to deprotonate a terminal alkyne? Explain.

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We are asked to explain this difference in acidity and explain if the cyanide anion (the conjugate base of HCN) can be used as a base to deprotonate a terminal alkyne.


a) ↓ pKa → ↑ Acidity


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The pKa of CH3NH2 is 40, while the pKa of HCN is 9.

(a) Explain this difference in acidity.

(b) Can the cyanide anion (the conjugate base of HCN) be used as a base to deprotonate a terminal alkyne? Explain.

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