Problem: Under basic conditions (catalytic MeO– in MeOH), compound 1 rearranges through the mechanistic sequence shown below to a propellane-type isomer 5 (J. Am. Chem. Soc. 2012, 134, 17877– 17880). Note that MeO– is catalytic in that it is consumed in the first step of the mechanism and regenerated in the final step. Provide curved arrows consistent with each mechanistic step and the resonance structure of 2 that is the greatest contributor to the resonance hybrid.    

FREE Expert Solution
Problem Details

Under basic conditions (catalytic MeO in MeOH), compound 1 rearranges through the mechanistic sequence shown below to a propellane-type isomer 5 (J. Am. Chem. Soc. 2012, 134, 17877– 17880). Note that MeO– is catalytic in that it is consumed in the first step of the mechanism and regenerated in the final step. Provide curved arrows consistent with each mechanistic step and the resonance structure of 2 that is the greatest contributor to the resonance hybrid.

Frequently Asked Questions

What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Major and Minor Resonance Contributors concept. If you need more Major and Minor Resonance Contributors practice, you can also practice Major and Minor Resonance Contributors practice problems.

What is the difficulty of this problem?

Our tutors rated the difficulty ofUnder basic conditions (catalytic MeO– in MeOH), compound 1 ...as high difficulty.

How long does this problem take to solve?

Our expert Organic tutor, Chris took 5 minutes and 43 seconds to solve this problem. You can follow their steps in the video explanation above.

What textbook is this problem found in?

Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 2nd Edition. You can also practice Organic Chemistry - Klein 2nd Edition practice problems.