Organic Chemistry II - Midterm 2008

Not by resonance with the ns lone pair only t h e o r

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, not by resonance with the N's lone pair. Only t h e o r t h o a n d p a r a - s u b s t i t u t e d i n t e r m e d i a t e s b e n e f i t f r o m t h i s a d d i t i o n a l r e s o n a n c e s t a b i l i z a t i o n w i t h t h e N ' s l o n e p a i r (see structure above) 1 meta-substituted 1 1 1
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Midterm Answers 6 of 11 8. Propose a synthesis of the following compound from benzene. Show all required reagents and intermediates. An analysis and retrosynthesis are not required. ( 11 points) Note: your synthesis must give the compound shown as the major product of the sequence. O Me NH 2 HNO 3 H 2 SO 4 NO 2 SO 3 H 2 SO 4 NO 2 SO 3 H these steps can be reversed NaOH Δ NO 2 OH NaOH (strong base) CH 3 I NO 2 O CH 3 Sn, HCl O Me NH 2 1 1 1 1 1 1 1 1 1 Order of reactions: 1 point - Both electrophilic aromatic substitutions before other reactions 1 point - Generate the phenol and methylate it BEFORE reducing the nitro group
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