Hello Chemistry Students! Your Tutor Jake here with an organic mechanism problem involving a resonance stabilized carbocation intermediate.
Here we have But-2-en-1-ol reacting with hydrobromic acid to first form a positively charged "water" molecule connected to our organic intermediate. The water molecule is a good leaving group and will leave the structure to generate our carbocation intermediate that is stabilized through resonance. We have both a primary and a secondary allylic carbocation resonance structures that will both react as electrophiles with the nucleophilic bromide ion. Once the bromide ion attacks either carbocation in the two structures, we have generated both products 1-bromobut-2-ene and 3-bromobut-1-ene successfully.
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Organic Chemistry Smith 5th edition problem 16-59