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Portmess Homework Q&S 75

Portmess Homework Q&S 75 - 69 ALCOHOLS AND ALKYL...

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4.7 Since the p K a of HCN is given as 9.1, its K a 10 9.1 . In more conventional notation, K a 8 10 10 . Hydrogen cyanide is a weak acid. 4.8 Hydrogen cyanide is a weak acid, but it is a stronger acid than water (p K a 15.7). Since HCN is a stronger acid than water, its conjugate base (CN ) is a weaker base than hydroxide (HO ), which is the conjugate base of water. 4.9 An unshared electron pair on oxygen abstracts the proton from hydrogen chloride. 4.10 In any proton-transfer process, the position of equilibrium favors formation of the weaker acid and the weaker base from the stronger acid and base. Alkyloxonium ions (ROH 2 ) have approximately the same acidity as hydronium ion (H 3 O , p K a 1.7). Thus hydrogen chloride (p K a 7) is the stronger acid. tert -Butyl alcohol is the stronger base because it is the conjugate of the weaker acid ( tert -butyloxonium ion). The equilibrium constant for proton transfer from hydrogen chloride to tert -butyl alcohol is much greater than 1. 4.11 The proton being transferred is partially bonded to the oxygen of tert -butyl alcohol and to chloride
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