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CHE 322 Exam 3 May 7, 2012 /100 Name 1. (10) Explain the difference between “hard” and “soft” nucleophiles. Give a structure of each kind that supports your description. 2. Predict the major product (3 pt each) NH trace H+ a. Br O anhydrous 1) b. EtOOC H2O EtO-, one eq. 2) COOEt Br drip in low conc in EtOH e. H+ O 1) EtO- OEt 2) EtO-, one eq. H+ H2O Br OEt (drip in) O 1) LDA g. O 2) 3) NaBH 4 4) H O 2 O Cl h. 1) Et CuLi 2 O 2) H O 2 hot dry 3. (8) Give the complete mechanism that shows why the reaction of butanal with a cyclic 2° amine followed by heating with acid produces an enamine that is nucleophilic at butanal’s former α-carbon. 4. Synthesize from any needed inorganic or specialty compound plus the indicated carbon sources: a. 2-heptanone from simple alcohols of 4 C or fewer. No strong base like LDA is available. (10 pt) COOEt from toluene and simple alcohols of 4 C or fewer (6 pt) b. Ph c. O from benzene (4 pt) 5. (4 each) What stable smaller compounds (that one could purchase) would you combine, and under what conditions, to make the indicated large compound? In each case show the reaction that makes the C-C or C-O bond that links the pieces. All three must be different kinds of reactions. [Caution: parts of some reaction partners are missing in the given products due to replacement or subsequent reactions during workup.] 6. (4 each) Say whether and why each of the following transformations is likely to succeed or fail in giving a decent yield of the indicated product. a. O O O EtO- O COOEt O ========================================================================= ========================================================================= c. O EtOOC EtO(one eq.) N 1) H+, H2O 2) hot COOH O 7. (8) Is alkylation of 1-aminobutane with 1-bromobutane using one equivalent of each to produce dibutylamine a good plan? Explain, giving all important reasons.