Lecture 15 - benzylic C-H bond Reduction of Aryl Ketones to...

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1 Reading for Monday ± Chapter 19: 19.1-19.3, 19.5-19.7 Third ARIS Quiz ± Available Now ± Due at 11:59 pm, Sunday, Feb. 27 ± Two attempts; Score will be average of the two attempts. Mon. 6:00-7:30 pm MAL 3092 Tues. 2:30-4:00 PM MAL 2007 Wed. 5:00-6:30 PM MAL 2001 Thurs. 9:30-10:50 AM MAL 1003 Sat. 11:30 AM-1:00 PM MAL 2007 PLUS Sessions Chapter 18 Electrophilic Aromatic Substitution Other Useful Reactions (18.13; 18.14) Some substituents added via EAS can undergo further transformations These extend the synthetic utility of EAS Fig. 18.7: Effect of substituents on benzene reactivity EAS followed by one or more other reactions Can be added via EAS
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2 Oxidation of Alkyl Benzenes (18.14A) Alkyl groups can be converted to carboxyl groups using KMnO 4 Alkyl group must have at least one
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Unformatted text preview: benzylic C-H bond Reduction of Aryl Ketones to Alkyl Benzenes (18.14B) • Acyl groups can be reduced to alkyl groups • Clemmenson reduction • Wolff-Kishner reduction • Indirect route to alkyl benzenes that cannot be prepared via Friedel-Crafts alkylation due to rearrangements Reduction of Nitro Groups (18.14C) • –NO 2 converted to –NH 2 , which cannot be introduced directly • We will consider two sets of reagents: • H 2 , Pd-C • Sn, HCl Benzylic Bromination (18.13) • Bromination at benzylic positions is highly selective, because benzyl radicals are resonance stabilized • Products are useful precursors for S N 2 and E2 reactions, which open up additional avenues for synthetic transformations...
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This note was uploaded on 10/24/2011 for the course CHEMISTRY 623 taught by Professor Benson during the Spring '11 term at Kansas.

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Lecture 15 - benzylic C-H bond Reduction of Aryl Ketones to...

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