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[1] (a) (6 pts) Propose a reasonable mechanism for the following reaction. D CONHE aq. NOH (b) (12 pts) Suggest reasonable sy
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[1] (a) The reaction involved in the converion of an amide to its 1o amine with 1 C atom less, is called Hoffmann bromamide reaction. The reaction mechanism is given below.

117 La) By , ་ , > = ཚཔོ། ༤ Rsཁ༧ས། O. 7 ་ : ཀྱིས ། བ - ཚེ ན ཀྱི ས 7 ། ༡༦༡ -NH2 H-

[1] (b) The synthetic route for compound (i) & (ii) are given below along with reagents.

[I] (b) 1. CHg Mg Br XI 2. 14/420 CH3 11.0304/py 22. NaHSO3 OH 09 TBDMSce E HO- midangle TBDMS Pec Ho 9 1. CH 3 Mg Br 2 HF/62Note:- TBDMSCl is Tert-Butyldimethylsilylchloride

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