Destroyer OChem question...AGAIN!

[kxb4777]

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Can someone explain why on roadmap 3, sodium tert-butoxide (i think that's what its called) and tert-butanol form a different double bonded Carbon than Potassium methoxide and methanol?

All I know is that ones a strong base and one is a bulky base, so they both undergo E2...Not sure if that plays into it.

 

[Cute Fairy]

Can someone explain why on roadmap 3, sodium tert-butoxide (i think that's what its called) and tert-butanol form a different double bonded Carbon than Potassium methoxide and methanol?

All I know is that ones a strong base and one is a bulky base, so they both undergo E2...Not sure if that plays into it.

t-butoxide it a big base and its hard to produce an elimination reaction with a more substituded alkene...while metoxide and butoxide are strong but small bases they are able to produce more substituded alkenes.

 

[Saber tooth]

t-butoxide it a big base and its hard to produce an elimination reaction with a more substituded alkene...while metoxide and butoxide are strong but small bases they are able to produce more substituded alkenes.

Cute Fairy is right, since the big base (t-butoxide with a spectator ion Na) cannot eliminate and produce more "substituded alkenes. Small bases always produce more stable alkenes...

Hope that helps

 

[levyusupov]

to add to what saber tooth and cute fairy said, t-butoxide react as to form E2 product by hoffman (less subsituted alkene) where all the other strong and not bulky bases form E2 product by Zaitsev (more subsituted alkene)