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Spring2011 CHEM224 Akira Kawamura Chapter 13A: Conjugated Unsaturated Systems A. Overview Today’s main goals: (1) Chemistry of allylic position, (2) Definition of conjugated systems Why important? (1) Allylic position has unique chemical reactivity that is frequently used in organic chemistry, (2) Conjugated systems have distinct spectroscopic and chemical properties. Key points: Allylic position: Why special? (13.3-13.5) Allylic halogenations (13.2) Cl 2 heat Cl NBS, CCl 4 ROOR or light Br N -bromosuccinimide (NBS) Br N O O (a) (b) Conjugated multiple bonds (13.6) s-trans s-cis B. Problem session (13.2) Draw the initiation, propagation, and termination steps of the following free radical reaction. Cl 2 ∆ Cl (13.2) What are the structures of A and B ?? NBS, CCl 4 h ν A (C 6 H 9 Br) B KOC(CH 3 ) 3 HOC(CH 3 ) 3 (C 6 H 8 ) (13.2-13.3) Propose the synthesis of target molecule (TM) from the designated starting materials (SM) and any necessary reagents. from
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