Organic Chemistry Practice Problems Hydrohalogenation Practice Problems Solution: Predict the product(s) or reagents of the followin...

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Solution: Predict the product(s) or reagents of the following reactions.

Problem

Predict the product(s) or reagents of the following reactions.

Solution

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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