Explain why the following bromoketone forms different bicyclic compounds under d

Question

Explain why the following bromoketone forms different bicyclic compounds under different reaction conditions O CH3 LDA/THF 78 °C LDA/THF 3 Br 0 °C At low temperatures the proton will be more apt to be removed from the methyl group, because its hydrogens are more acidic (that is, the thermodynamically controlled product will be formed). At higher temperatures, the proton will be more apt to be removed from the ?-carbon, because its hydrogen is the most accessible. Thus, the kinetically controlled product is formed At low temperatures the proton will be more apt to be removed from the ?-carbon, because in that way the more stable enolate is formed (that is, the kinetically controlled product will be formed). At higher temperatures, the proton will be more apt to be removed from the methyl group, because its hydrogens are the most accessible and are slightly more acidic. Thus, the thermodynamically controlled product is formed At low temperatures the proton will be more apt to be removed from the methyl group, because its hydrogens are the most accessible and are slightly O more acidic (that is, the thermodynamically controlled product will be formed). At higher temperatures, the proton will be more apt to be removed from the a-carbon, because in that way the more stable enolate is formed. Thus, the kinetically controlled product is formed At low temperatures the proton will be more apt to be removed from the methyl group, because its hydrogens are the most accessible and are slightly more acidic (that is, the kinetically controlled product will be formed). At higher temperatures, the proton will be more apt to be removed from the ?- carbon, because in that way the more stable enolate is formed. Thus, the thermodynamically controlled product is formed. O

Explanation / Answer

Undoubtedly, the correct answer is option 4.

Explanation: At low temperature (-78 oC), kinetically controlled product (5,7-fused bicyclic compound) will be formed, whereas at high temperature (0 oC), thermodynamically controlled product (5,5-fused bicyclic compound) will be formed.

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