1.

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. Arrange the following amides according to their relative reactivity when react with Br_2 in excess of strong base

Answer»

IVgtIgtIIgtIII
IIgtIgtIIIgtIV
IIgtIVgtIIIgtI
IIgtIgtIVgtIII

Solution :Electron donating GROUPS, ACCELERATES the process of REARRANGEMENT & electron with DRAWING groups retard it.


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