Orgo Destroyer #182 question

[ScarletKnight24]

Advertisement - Members don't see this ad

The answer key said C because it is a bulky base so it will undergo E2 with less substituted alkene.

My question is that isn't there only ONE beta carbon where you can grab the hydrogen from? so the answer should also be b, d, and e correct? They are all strong bases and are capable of doing E2.

How can you pick and choose where the double bond forms if there is only one beta carbon?😕

 

[lutopie0730]

The answer key said C because it is a bulky base so it will undergo E2 with less substituted alkene.

My question is that isn't there only ONE beta carbon where you can grab the hydrogen from? so the answer should also be b, d, and e correct? They are all strong bases and are capable of doing E2.

How can you pick and choose where the double bond forms if there is only one beta carbon?😕

First, yes, they are all capable of doing E2. BUT there would be SN2 reactions and you will get mixture of substitution product and elimination product.
Second, if the base is bulky, then it would favor elimination over substitution.

Therefore, the best reagent (base) for E2 is a bulky base, answer c

 

[ScarletKnight24]

First, yes, they are all capable of doing E2. BUT there would be SN2 reactions and you will get mixture of substitution product and elimination product.
Second, if the base is bulky, then it would favor elimination over substitution.

Therefore, the best reagent (base) for E2 is a bulky base, answer c

OH yes you are right. By using bulky base then for sure my product will be E2. Can't believe I overlooked that. Thanks.