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As the figure in this webpage says, at low temperatures, the major product of hydrohalogenation of 1,3-butadiene is the kinetic product, the 1,2-addition product. At high temperatures, the major product is the thermodynamic product, the 1,4-addition product, in which the pi electrons have transferred to the inner carbon skeleton to form a more substituted alkene product. The carbocation rearranged due to resonance.

However, as the figure below from David Klein's Organic Chemistry 2e book tells us--the major hydrohalogenation product of 3-methyl-1-butene is the rearrangement product, which is the more stable product. Here, the carbocation rearranged due to its inherent stability at highly substituted carbons. The temperature of the reaction was not specified.

hydrochlorination of 3-methyl-1-butene

My questions are:

  • Is it safe to assume that the hydrochlorination of 3-methyl-1-butene give a product ratio as shown in the figure at all temperatures (except at temperatures where decomposition may occur, if it can)?
  • Do alkene addition reactions also have thermodynamic and kinetic control, like the butadiene reaction exhibited, or is the thermo and kinetic product production only due to resonance?
  • Can carbocation rearrangements have kinetic and thermodynamic products, like the one for the hydrohalogenation of butadiene?
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closed as unclear what you're asking by Jan, Mithoron, Zhe, pentavalentcarbon, Tyberius Sep 22 '17 at 14:30

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  • $\begingroup$ These are fundamentally different. Resonance isn't a "rearrangement". $\endgroup$ – orthocresol Sep 22 '17 at 11:55
  • $\begingroup$ Confused by title. Being under thermodynamic control implies not being under kinetic control. $\endgroup$ – Zhe Sep 22 '17 at 13:40