1 Propose a synthesis from bromobenzene and any materials with 4 carbons or less a possible solution not discussed in class O 1 nBuBr Na2Fe CO 4 2 PPh3 3 O Pd 0 K3PO4 Br Br 2 Indicate the formal oxidation state of the metals in each complex O BF4 N N N OH2 Cu OH2 N O N Cu Ni O N O Zr OPh 2 Zr OPh 2 Zr IV Zr II Cu I Cu II Ni II 3 Predict the product Explain with a detailed mechanism Pd PPh3 4 or D I D H Pd 0 oxidative addition H syn B hydride elimination alkene insertion D PdI H D syn PdI H I Pd D Pd HI 4 Ethyl benzoate is straightforward For benzoic acid O O MeLi O OH MeLi O O Me Dianion is stable until workup H3O O HO OH Me Me LDA enolizes the intermediate ketone Thus it cannot react further with MeLi O CO2Me MeLi LDA OLi CH3 H O Me does not react with MeLi
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