Question

2. Examine the following Electrophilic Aromatic Substitution reaction. 1) Provide the number of 13C NMR signals expected in both the reactant and the product. 2) Provide the carbocation intermediate that allowed the transformation to happen at that position. 3) This molecule is (ortho, meta, para) substituted (circle one). 4) Using resonance arrows show how that carbocation can be distributed (delocalized) to multiple locations on the arene ring system. 5) Predict a different structure that can form from this delocalization. FeBrg, Brz # of "C NMR signals # of 13C NMR signals Key C. intermediate Resonance Structures Other possible product 3. Predict the # of unique C NMR signals for the following molecules and reaction H, Pd # of "C NMR signals Name these two compounds # of 13C NMR signals # of SC NMR signals # of 13C NMR signals Is this E/Z?

Answer 1

3 By 672 Fe Brz Br2 Ć NO # ok 13C NMRY C Signals sonale Key c he mediate 3 This molecule is ortho) substituted.

BV Resonance structures. Wed 10 Br Other possible prodnict

Thu 11 - Thu i 3 B 3 . # 13C NMR 6 9 # of 13C NMR signals 2-chloro-3,4-dimethyl -pentane signals 2, 3,4-trimethul pentane E s l H2 g Pd. # of 13 # of " (NMR 4 NMR Fri 12 signals. Neither E nov z signal.