Heating the oxetane below to 560°C gives two products A and B (Scheme 2) A + CI Oxetane Scheme 2 The spectroscopic data for A and B is as follows. A - IR 1640cm1, m/z 138 (100%), 140 (33%); dH (ppm) 7.1 (4H,s), 6.5 (1H, dd, J= 17, 11HZ), 5.5 (1H, dd, J= 17, 2Hz), 5.1 (1H, dd, J= 11, 17HZ). B- IR 1700cm1, m/z 111 (45%), 113 (15%), 139 (60%), 140 (100%), 141(20%), 142 (33%); dH (ppm) 9.9 (1H, s) 7.75 (2H, d, J = 9Hz), 7.43 (2H, d, J = 9Hz). a) Suggest the structures for both products A and B. b) Show the mechanism by which they may be formed.

Heating the oxetane below to 560°C gives two products A and B (Scheme 2) A + CI Oxetane Scheme 2 The spectroscopic data for A and B is as follows. A - IR 1640cm1, m/z 138 (100%), 140 (33%); dH (ppm) 7.1 (4H,s), 6.5 (1H, dd, J= 17, 11HZ), 5.5 (1H, dd, J= 17, 2Hz), 5.1 (1H, dd, J= 11, 17HZ). B- IR 1700cm1, m/z 111 (45%), 113 (15%), 139 (60%), 140 (100%), 141(20%), 142 (33%); dH (ppm) 9.9 (1H, s) 7.75 (2H, d, J = 9Hz), 7.43 (2H, d, J = 9Hz). a) Suggest the structures for both products A and B. b) Show the mechanism by which they may be formed.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter15: Benzene And Aromaticity

Section15.SE: Something Extra

Problem 29AP: 3-Chlorocyclopropene, on treatment with AgBF4, gives a precipitate of AgCl and a stable solution of...

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