Orgo, destroyer..??

[JDHK]

I feel like im right on this one..This is obviously E2 reaction with the adjacent carbon losing a hydrogen, but there are no other adjacent carbons other than that one. Do E2 reactions do rearrangements too?? The answer is the T-butyl (C), which I know is anti zaitsev in E2 reactions, but why would there be a need for anti zaitsev when there is only one adjacent carbon with hydrogens. Unless it rearranges to 2 carbons away somehow..? I felt the answer was OH-, the strong base and strong nucleophile that would result in E2 per usual.

 

[hope_to_match]

the answer is t-butyl, because this is the only way to get the least substituted alkene...

 

[JDHK]

the answer is t-butyl, because this is the only way to get the least substituted alkene...

I'm aware of that, but there is no "more substituted" alkene to compare to isn't there? There is only one possible alkene here, so why would u need to specify a reagent to get anti zaitsev..? Bromine is in the end carbon, and there isn't any rearrangements in E2 reactions

 

[hope_to_match]

because in order to form the anti zaitsev you need to have a very bulky base. if you were to use an -OH with a primary bromine, the reaction would go SN2 and Br would be substituted for OH in the primary position with inversion of configuration and all that good stuff..

since you see that your product is the least substituted alkene, you right away know that a bulky base was used

 

[hope_to_match]

look at chad's notes and draw out products using every answer choice you will see that t-butyl is the only one that will have E2 in that position. Other reactants will undergo substitution, not elimination

 

[JDHK]

True that. Thank you!

 

[hope_to_match]

You are welcome 🙂