Problem: Predict the major organic product of the following reaction:When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.

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We’re being asked to determine the product 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

Predict the major organic product of the following reaction:

When drawing hydrogen atoms on a carbon atom, either include all hydrogen atoms or none on that carbon atom, or your structure may be marked incorrect.