Problem: Draw a structural formula for the more stable carbocation intermediate formed in the reaction shown. 

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We’re being asked to draw the more stable intermediate of the given reaction.



Recall that alkenes are converted to alkyl halides via hydrohalogenation, which occurs in two steps:

(1) protonation – the alkene is protonated, forming a carbocation intermediate and a halide ion. This follows Markovnikov’s rule, which states that the more stable carbocation is formed.


Also, since a carbocation is formed during the reaction, the carbocation may rearrange into a more stable one.


(2) nucleophilic attack – the halide ion comes in and attacks the positively-charged carbon. The stereochemistry for this reaction is unknown since the nucleophile can attack either side of the empty p-orbital.


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Problem Details

Draw a structural formula for the more stable carbocation intermediate formed in the reaction shown. 

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Based on our data, we think this problem is relevant for Professor Pflum's class at WAYNE.