Question

(14) [4 points] The compound in the figure undergoes E2 elimination much more slowly than one would expect a 3? alkyl halide to do. (Yes, it is the same compound as in the other question.) Why? (You may want to rotate the structure in 3D to see it better. If you do, click on the image, copy the code, navigate to a page with a MarvinJS window, paste the structure into the window, press the Clean 3D button, and press the Rotate in 3D button.) Launch-MarvinView™ or click image to copy source

Answer 1

The E2 elimination reaction is proced throught the alkene nature intermediate the alkene is the trigonal palnnar and sp² hybridized carbon atom but in the above structure the bromine atom is present at bridging position this bridging possition does not give the formation of plannar alkene intermediate readily because the bridging position is non-plannar (this non - plannarity is depends on the bridging possition of both carbon atom) atom therefore E2 elimination reaction is very slow