We are asked to determine both the 1,2 and 1,4 products of the reaction below.
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.
However, we have 2 consecutive double bonds which make this a conjugated hydrohalogenation.
1. Draw the addition products formed when one equivalent of HBr reacts with 2,4-hexadiene. (Draw a single product for each.)
1, 2 product addition
1, 4 product addition
2. Draw the addition product formed when one equivalent of HCl reacts with the following diene.
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