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exam4_blank - 1 Chemistry 322b – Fall 2011...

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Unformatted text preview: 1 Chemistry 322b – Fall 2011 Practice Exam IV Section I. Multiple Choice. 1. The directed crossed aldol condensation of I and II below is best promoted by which procedure below. O O O + I II A. Adding I slowly to a heated aqueous basic solution of II. B. Reacting a mixture of I and II in the presence of acid with heating. C. Reacting I with LDA and then adding II. D. Reacting I with nBuLi and then adding II. 2. Circle the reaction or reactions below that is/are likely to lead to the isolation of the self ­aldol addition product. O H dilute NaOH / H2O CH3 O H3C dilute NaOH / H2O CH3 O H 5 oC dilute NaOH / H2O CH3 O H3C 5 oC 50 oC dilute NaOH / H2O CH3 50 oC 2 3. Circle the compound or compounds below that will favor conjugate addition to an α,β unsaturated ketone. Li CH3CH2MgBr (CH3CH2)2CuLi O O N Na 4. Rank the following compounds from the most acidic to the least acidic. NH3 II O NH2 I OH III II > I I > III IV > I I > II > > > > IV III > IV II > IV II > III IV > III Section II. Complete the Reaction. 5. O H H NaOEt EtOH / heat O 3 6. O H + CN NaOCH2CH3 CH3CH2OH heat 7. A A NH2 4 8. O A O O A H3O+ B 5 9. NH2 A A B Br B I Br 6 Section III. Draw the Mechanism. 10. Draw the complete “electron ­pushing” reaction mechanism for the transformation below. Make sure to show all steps. O O O O 1. NaOEt O O O 2. H+ 7 Section IV. Synthesis. 11. Outline an efficient synthesis for the product below using the indicated starting material and any 1 ­4 carbon sources. O O O O 8 12. Outline an efficient synthesis for the product below using the indicated starting material and any 1 ­4 carbon sources. OMe ...
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