252 exam 1 - 1. (8 Points, 2 points each box) Give the...

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Unformatted text preview: 1. (8 Points, 2 points each box) Give the correct name for the following compounds. OCH2CH3 a) NH2 OH b) O O c) H d) O 1 2. (6 Points, 2 points each box) Draw the correct structures of the following compounds. a) Valeraldehyde c) isopropyl phenyl ketone c) 4-cyclooctenone 3. (4 Points, 1 point each) Mark each of the following compounds as aromatic (A) or not aromatic (NA). O H N a) N H b) c) d) 2 4. (8 Points) Draw all contributing resonance structures for the following ions. Br 4 Points a) NO2 NH 4 Points b) 3 5. (4 points ) Encircle the strongest base among the following: S S NO2 S OCH3 S CH3 A B C D 6. (8 Points) Show a stepwise mechanism for the following electrophilic aromatic substitution reaction and write the structure of the major and the minor products in the appropriate boxes. Cl + AlCl3 Major Product 2 Points Minor Product 2 Points (4 Points) Show stepwise mechanism for the formation of the two products. 4 7. (8 Points) Propose the structure for Compound A that has the following 1HNMR spectrum. Molecular formula of Compound A: C10H13 BrO IR: 1150 Cm-1 1 HNMR d 7.1, doublet, 2 H d 7.4, doublet, 2 H d 3.8, singlet, 3 H d 3.5, triplet, 2 H d 2.7, triplet, 2 H d 1.9, quintet, 2 H Compound A 5 8. (6 Points, 3 point each box) Complete the following Willamson ether synthesis. 1) K An Alkoxide ion 2) O 9. (6 Points, 3 points each) Complete the following Grignard reaction. OH 1) PBr3 2) Mg, ether HO 6 10. (20 Points, 5 Points each) Outline an efficient synthesis for each of the following compounds starting with the given starting material and any suitable reagents. Br ? a) NH2 O H3CH2C ? b) OCH2CH3 7 O ? c) CO2H O O HO CN O d) H C 3 ? H H3C H 8 11. (24 Points, 2 points each box) Complete the following chemical reactions by filling the boxes with reagents, reactants, or products. For products, only give the major organic ones. O 1) NaBH4 a) 2) H3O 3) POCl3, Pyridine 4) PhCO3H 5) PhCH2MgBr 6) H3O 7) SOCl2 8) Mg, ether 9) H2C 10) H3O O (formaldehyde) 9 OH 1) Tos Cl 2) CH3CH2SNa b) O c) SO3H d) I2, CuCl2 2) NaOH, H2O, 3) H3O O e) PhNHNH2 H 10 f) KMnO4, H2O, O OCH3 CH2OH g) 11 ...
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This note was uploaded on 04/09/2008 for the course CEM 252 taught by Professor Rathke during the Fall '08 term at Michigan State University.

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