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Hofmann rearrangement In the Hoffmann rearrangement an unsubstituted amide is treated with sodium hydroxide and bromine to give a primary amine that has one carbon lesser than starting amide. R-oversetoverset(O)(||)C-NH_2+NaOH+Br_2toR-N=underset("isocyanate")(C=O)overset("hydrolysis")toR-NH_2 Mech : If the migrating group is chiral then its configuration is retained . Electron releasing effects in the migrating group increases reactivity of Hofmann rearrangement. Which of the following compound cannot give Hofmann rearrangement : |
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