Unformatted text preview: 1. (8 Points, 2 points each box) Give the correct name for the following compounds.
O O a)
Ph O Ph O b) CO2H O c)
N(CH3)2 O d)
H O 1. (6 Points, 2 points each box) Draw the correct structures of the following compounds. a) Pyrrole b) isobutyl acetate c) 4-chloroheptanenitrile 1 2. (4 Points) Draw all possible resonances for the enolate that is formed in the following reaction.
O O NaOCH2CH3 3. (4 Points, 2 points each) Arrange the following amines from the most stable to least stable one. Assign numbers of 1 through 4 to the following compounds (1 = most stable base, 4 = least stable base).
NH2 NH2 Cl NH2 OCH3 NH2 NO2 4. (8 Points) Propose the structure for Compound B that has the following 1HNMR spectrum. Molecular formula of Compound B: C4H7ClO2 IR: 1730 Cm-1, strong, 3100, broad, strong
1 HNMR d 11.6, singlet, 1 H d 4.2, triplet, 1 H d 2.1, quintet, 2 H d 1.1, triplet, 3 H Compound B 2 5. (6 Points, 3 points each box) Fill in the boxes with the starting monomers needed to synthesize the following polyamide. + O
* O C H N H N n
* C 6. (8 Points) Provide a stepwise mechanism for the following Intramolecular Claisen condensation (Dieckmann) reaction. O O 1) NaOCH3
H3CO OCH3 2) H3O, Heat 3 7. (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.
O O H2N a) ?
OEt Ph O O OH ? b) EtO
OEt C H CH3 4 O H ? c)
H O N O CO2H d) ? 5 8. (8 Points) Give the product for the following hydrolysis reaction and provide a stepwise mechanism for it. O Ph H2O, H
NH2 Heat 4 Points Mechanism (6 Points): 6 9. (28 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. a) 1) CrO3, H3O OH 2) SOCl2 3) CH3OH, Pyridine 4) 2 CH3CH2MgBr 5) H3O b)
Ph O 1) LiAlH4 OH 2) H3O 3) SOCl2 4) NaCN 5) LiAlH4 6) H3O O O O 7 c) Ph O 1) SOCl2 OH 2) 2 NH3 3) SOCl2 4) PhCH2MgBr 5) H3O O d) Ph OH 1) PBr3, Br2 2) H2O O e) 1) Br2, HBr 2) (CH3)3OK 3) NaCN 4) H3O , Heat 4) SOCl2 5) Ph2CuLi 8 9 ...
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- Fall '08
- Hydronium, Amide, following compounds, Intramolecular Claisen