1 Chem 2320 Exam 3 March 31, 2006 Name: (Please print) (first) (last) Last 4 digits of Banner No. Score I. Multiple Choice ( /20) /60 II /20 III /20 Total score /1002 I. Multiple choice questions. (3 points each). Please put your answers on Scantron sheet. Your score will be graded based only on your answers from Scantron sheet. 1. What is the name for the following compound? (a) acetyl acetyl anhydride (b) acetic anhydride (c) ethanyl anhydride (d) ethanoate anhydride (e) None of the above 2. What is the name for the following compound? (a) (E)-N-ethyl-3-pentenamide (b) (Z)-N-ethyl-3-pentenamide (c) (E)-N-ethyl-4-pentenamide (d) (Z)-N-ethyl-4-pentenamide (e) None of the above 3. What is the name for the following compound? (a) N-ethyl-N-methylacetamide (b) N-isoproplacetamide (c) N-ethyl-N-methylpropanmide (d) N-ethyl-N-methylethylamide (e) None of the above 4. What is the name for the following compound? (a) ethyl 4-oxopentanoate (b) ethyl ester methyl ketone (c) ethyl 4-ketonepentanoate (d) ethyl 4-ketone pentyl ester (e) None of the above H3CCOOOCH3 ONHC2H5 CNO OOO3 5. What is the structure of 2,6-hexanedione? 6. What could be the product for the following reaction? O1. CH3MgBr2. H+, H2Oproduct?(a)OH(b)OH(c)OHHH(d)OOH(e) None of the above 7. What is the order of increasing boiling points (from the lowest to highest) for the following compounds? NH2OIClOIIOHOIII (a) I, II, III (b) II, III, I (c) I, III, II (d) III, I, II (e) None of the above OO(a)HOO(b)O(c)(d)(e) none of the aboveOOO4 8. What could be the reagent and reaction condition for the following transformation? OCH3OCH2CH3CH3H3CH2CO? (a) ethanol, NaOH (b) ethanol, H+ (c) methanol, NaOH (d) methanol, H+ (e) None of the above 9. What should be the product from the following reaction? OOH1) NaBH42) H+, removal of waterHOOH(a) (c)product(e) none of the aboveOH(b)OOHOO(d)OHOH 10. What could be the product for the following transformation? OOCH31) CH3CH2MgBr(2 equivalents)2) HCl, H2OOOHOH(a)(b)OH(c)O(d)(e) none of the aboveproduct 11. What should be the product from the following reaction? OCH31) NaCN2) H+, H2O, heat(a) (b) (c)(d)(e) none of the aboveProductCH3OHCO2HCNOCH3OHCNCH3OHCH2NH25 12. What could be the product for the following reaction? product?OH1. NaBH42. H+, H2O(a)OH(b)OH(c)OHHH(d)OOH(e) None of the above 13. What could be the product for the following reaction? OOH1) SOCl22) CH3CH2OH(a) (b) (c)(d)(e) none of the aboveOCH2CH3CH3H3CH2COProductCH3OOCH2CH3OOCH2CH3CH3 14. What could be the products for the following reaction? OCH2CH3 H+, removal of waterProductsNH+NNINIIIIIN NIV (a) I, II (b) I, II, IV (c) III, IV (d) II, III (e) None of the above6 15. What could be the product for the following reaction? NOOBr1)2) H+, H2O, heatNH3OHIproduct ?IIIIINOOIVHV (a) I (b) II (c) III (d) IV (e) V 16. What could be the product for the following reaction? OCH3CH3NH2H+, removal of waterNCH3CH3Product ?NHCH3OOHONHCH3CH3I IIIIIIVH3CHN (a) I (b) II (c) III (d) IV (e) None of the above7 17. What could be the reagent for the following reaction? O1) reagent(a) CH3MgBr(e) none of the aboveO(b) (CH3)2CuLi(c) Ph3P(d) CH3BrPh = C6H5H3C2) H+, H2OCH2 18. What could be the reagent for the following reaction? COH(a)(b)(c)(d)(e) none of the aboveProductCH3CCHOOCH3POEtOEtOCOHHCH3CCHCH3CCOOCH3HCHCH3CCOHHCHCH3CCOHHHH8 19. What could be the product for the following reaction? OOCH3H+removal of waterOHHSSHH2Raney NiProduct ?OHOHIOOCH3IIOCH3IIIOOCH3HIVS S (a) I (b) II (c) III (d) IV (e) None of the above 20. What could be the product for the following reaction? 1. NaBH42. H+, H2OOOOHC(CH3)3Product ?IOOOHC(CH3)3OOOHC(CH3)3OHOHIIIIIOHOHIV (a) I (b) II (c) III (d) IV (e) None of the above Continue to the Next page9 II. A synthesis for the preparation of compound 6 is proposed as below: 1. Please provide an electron-pushing mechanism for the formation of compound 3 from compound 1 (reaction 1). (16 points) Continue to the Next page OMeOOOOH+H2OOMeOOHHOCH3MgB r(2 equivalents)H+OOOHH+H2OOHHOOHO1356242(Re action 1)(Re action 2)(Re action 3)10 2. The proposed synthesis involves protection (reaction 1), nucleophilic addition (reaction 2), and deprotection (reaction 3). Will you expect to obtain the same final product, compound 6, if compound 1 is treated with the Grignard reagent, 4, (reaction 2) without going through the protection (reaction 1) first? Explain briefly your reason. (4 points) Continue to the Next page11 III. Propose an electron pushing mechanism for the following reaction. You have to show how to form the hydrazone intermediate. (20 points) OH2NNH2KOH,