orgo #80 in Destroyer

[hmm_think]

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in destroyer #80 orgo section...
After step #1 why doesnt the (ch3)3co-k+ do a 2-3 elimination that makes it more substituted?
Answer says it goes 1-2 elimination.

Thanks guys

 

[dentstd]

call Dr. R. Call him now. it's 2 am his time.

 

[How Sleepy??!!]

Hey, you don't have to call Dr. Romano for this one...here's the answer...

After adding the SOCl2 we have created a secondary halide. Secondary halides are susceptible to both more substituted elimination and less substituted elimination, depending on the base used. If the base is an ordinary strong base (NaOC2H5 etc...) then a more substituted elimination results. However, if the base is strong, big and bulky (such as (CH3)3COO-Na+), then due to steric factors it must do elimination to "the outside," thereby forming the less substituted elimination. If you look at the question, you will notice that the , strong, big and bulky base was used, and therefore the less substited alkene was formed.

I hope this helped!! Good luck!!