oChem question!!!!

[O Gaúcho]

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Please help me to understand why this would not be an SN2 reaction. My teacher marked me off and said the major product is an E2 product. Thanks for the help!

 

[O Gaúcho]

@orgoman22

 

[iliketeeth13]

I believe that the protic solvent plus the tertiary halide makes E2 the reaction that will more likely happen. SN2 would be pretty much impossible on such a hindered carbon.

 

[DAT Destroyer]

Look at the starting material.....This is a tertiary halide with an excellent leaving group. Tertiary halides LOVE to do the E2 reaction, especially when strong nucleophiles such as methoxide, ethoxide, amide, or hydroxide are employed. Here....you are using methoxide on a tertiary halide, thus E2 would indeed be the major product. I would say 85% E2 with 15% Sn2 minor,,,,and I am being generous towards Sn2.

I hope this helps.

Dr Romano