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OpenStudy (anonymous):

which of the following reagents not convert butan-1-ol into chlorobutane? a) NaCl b) HCl c) SOCl2 d) PCl5

OpenStudy (anonymous):

I think a) is the right answer. I'm almost sure both SOCl2 and PCl5 are used as chlorine "donors" to alcohols. I doubt that NaCl would react as Na+ is more stable with Cl- than with OH- ions in solution. Plus: the H+ provided by the HCl can form water with the OH group and that leaves the carbocation free to react with the Cl-.

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