Why can hydroxide behave as a leaving group in this reaction?
Added by Sandra C.
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Hydroxide is a strong base and can act as a nucleophile, but it can also behave as a leaving group under certain conditions. Show more…
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Why is the pyrophosphate group necessary for nucleophilic substitution in the cell? What makes it a good leaving group? The hydroxy group of a metabolite is activated by its conversion to a pyrophosphate; Pyrophosphate's leaving group ability is favored by its electronegativity. The hydroxy group of a metabolite is activated by its conversion to a pyrophosphate; Pyrophosphate's leaving group ability is favored by its electronegativity. A high concentration of a strong acid is not available to a cell, and nucleophiles in the cell that react with activated OH groups are often amines. Pyrophosphate's leaving group ability is favored through the size of the leaving group. The hydroxy group of a metabolite is activated by its conversion to a pyrophosphate; Pyrophosphate's leaving group ability is favored through electron delocalization.
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An alcohol hydroxyl is a poor leaving group but a) a tosylate (ArSO2-) can displace it or b) a Bronsted-Lowry acid can be used to protonate it.
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Which molecules contain good leaving groups?
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