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Unformatted text preview: 1 7 - 1 8 continued (c) ( d) HO - CHCH3
I + + B F3 -- CHCH3
I C H3 CH3 1 7 - 1 9 In (a), (b), and (d), the electrophi le has rearranged. (a) CH 3 -c
I CH C H3 U
_ (b) ( c) No reaction : nitrobenzene i s t oo deactivated for the F ri edel C rafts reaction to succeed. (b) (c) (d) (e) gives desired product gi ves desired product, plus ortho i somer; use excess bromobenzene to avoid overalkylation gives desired product, plus ortho i somer gi ves desired product ~ p lus over-alkylation products 1 7-2 1 (a) (excess) (b) 0 0 ( CH3hCCI
• AICI3 C H3I
• A ICI3 (excess) 6 6 C(CH3h HN03
• H 2SO 4 S03
• H 2SO 4 3 74 ¢ ¢ C(CH3 h ( separate from o rtho, a lthough steric hindrance would prevent much o rtho s ubstitution) N0 2 (separate from o rtho) S03H ...
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