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Ch 21 answers - 1 Answers Ch 21 Extra problems Chem 345 SFN...

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1 Answers, Ch. 21 Extra problems Chem. 345, SFN 1. Show the major product (or products if more than one will be formed in significant amount) for the following reactions: Cl H CH 3 CH 3 1. Heat, O 2 2. H 2 SO 4 Cl OH O + After step 1 have the cumyl hydroperoxide. This is just like the parent (sect. 21.4b.3) a. H 3 C O H b. 1. KOH 2. BrCH 2 CH=CH 2 3. heat H 3 C O H This is a Claisen rearrangement O O Cl Cl Cl Cl c. NaOEt (2 equivalents) O O Cl EtO Cl OEt heat (two Michael addition, elimination reactions. The ethoxy group deactivates the C=O to which it is β ( π electron releasing effect) but it activates the one to which it is α (by an inductive effect in the σ framework), so the substitution pattern seen is that shown. O O Cl Cl Cl Cl d. NaCN (2 equivalents) O O Cl NC NC Cl heat this is "DDQ" The electron-withdrawing CN group activates the double bond on which it is substituted, producing the opposite substitution pattern. ( These reactions were cut from this edition of your text. I would no longer ask them. ) 2. Show regents and any intermediate compounds that would be isolated for the following
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