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Why would the concentrated hydrobromic acid be an inappropriate catalyst for the dehydration of alcohols?
a) HBr is too weakly acidic to protonate the alcohol.
b) The conjugate base, Br - , is a good nucleophile and it would attack the carbocation to form an alkyl bromide.
c) HBr is strongly acidic, so the water molecule would not be a good leaving group after protonation of the alcohol.
d) HBr would be more likely to promote rearrangement of the carbocation intermediate.
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Based on our data, we think this problem is relevant for Professor Anglin's class at ARIZONA.