Exam_2_06 - .—L Spring 2006, CEMZSZ Exam 2 (100 Points)...

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Unformatted text preview: .—L Spring 2006, CEMZSZ Exam 2 (100 Points) 1. (6 Points, 2 points each box) Give the correct structures for the following compounds. a) Acetaidehyde b) Benzyl Phenyl ketone c) 2,4—dimethyl-3-pentanone 2. (6 Points, 2 point each) Give the proper systematic or common name for each of the following compounds. b) CH3CH2COZCH2Ph _ 3. (4 Points) The pKa values of oxaloacetic acid are 2.22 and 3.98. Assign each pKa value to the corresponding carboxyl group. O pKa O pKa HO OH O 4. (8 Points, 2 points each box) In the boxes provided, answer the following questions about 2—pentanone. A) What is the pKa value of the most acidic hydrogen 0f 2—pentanone? B) Draw the two resonances of the enolate of 3—pentanone. LDA 3-Pcntanone —I- 4—... C) Draw the 2,4—dinitrophenylhydrazone derivative of 3-pentanone. 5. (4 Points, 2 point each) Estimate the pKa value of the most acidic hydrogen for each of the following compound. You shall get credit for this question if you are within 2 units of the literature value. OH 0 o EtOMOEt pKa 6. (12 Points, 3 points each box) Complete the following chemical transformations. An alkyl halide An ester 2) H+ CO CH 1) CHgONa b) HscOZCm 2 3 2) H+ 1) 2 CH3CHZSH, H+ 2) Raney Ni 7. (24 Points, 6 point each) Outline an efficient synthesis for the following starting with the given starting material and any other necessary reagents. O 7 OH 0 HSCHQCHC 33) —>- CH2CH3 QM d) _HO O __—_—...? M OCHQC H3 OH OCH3 Ph HO 8. (10 Points) Provide a stepwise mechanism for the following Claisen condensation reaction. 0 ML 1) CH3ONa OCH3 —"* + 2) H3O, heat (26 Points, 2 points each box) Complete the following reactions by filling the boxes with the appropriate reagents, reactant(s), or product(s). For the products, only include the major organic products. 0 o M 1) CH3ONa a) H ph "—" 2) PhCHzCHZBr + 3) HOCHZCHZOH, H .4— 4) NaBH4 5) H3O+ mic-l O + C) )k/ 1) CH3CH2NH2,H W 2) Pd, H2 OF‘h 0 d) A/“\ e) + CL “30 —h— 0 OCHS (H20, H+) O 1) mm, HCl CH3 —> f) 2) H3O+ H N o 1) LiAll—i4 ——-——P g) U 2) H20 NaOl—I ——> i ) P“ H20, Heat 0 O Ci? + Hk L0H H20, Heat 0 1)PB B r, r k Am 4 )HO 2)H20 0 no ,H+ 1) F,th fl + 3) H20, H ...
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Exam_2_06 - .—L Spring 2006, CEMZSZ Exam 2 (100 Points)...

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