(2+2 marks) corresponding Wheland result from bromination metato CHo group. Use
ID: 520803 • Letter: #
Question
(2+2 marks) corresponding Wheland result from bromination metato CHo group. Use these to explain why bromination of toluene is more likely to give 2-bromotoluene (the ortho isomer) than 3bromotoluene (the metaisomer). (8 marks) (d) Both C(CH3) and CH20H20CHsare onthapara directinggroups, However nitration of CeHsC(CH3) gives mostly the paradisubstituted product while nitration of CeH5CH12CH20CH gives mostly the ortho disubstituted product COCH,), (CH), NO2" main organic product CH/CH OCH, CH CH OCH NO2 main organic NO2 product Explain these two contrasting observations. (3 4 marks) Continued...Explanation / Answer
C. CH3 group is ring activating group(EDG) and directs the newly incoming electrophile (here Br + ) towards ortho / para positions.
D. This time tertiary butyl group is too bulky, so there is strong steric crowding b/n this and newly coming E+ . So,in this case we will get p isomer as major.
In another reaction there is no steric crowding, so ortho isomer is major.
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