Chem final exam

Chem final exam - NAME 810# first last, CHEMISTRY 2212...

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Unformatted text preview: NAME 810# first last, CHEMISTRY 2212 Final Exam May 5, 2009 Be sure to read each question carefully. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luck!! 1. (12 points) Describe a synthesis for 4-methoxyaniline starting from benzene and using any necessary reagents. For full credit you must draw all intermediate compounds and all reagents. ? - . Q —'|" H2N O 3 4-methoxyaniline 2. (12 points) Using the curved arrow formalism, provide a stepwise and detailed mechanism for the following reaction. (Hint: the mechanism involves carbocation intermediates; use H2804 for all protonation steps and SO42" for all deprotonation steps.) (1% 0. H2804 10. Bonus: Total: SCORE 2 3. (12 points) Circle the structure that best answers each question below. a. Which of the following would be the most reactive towards electrophilic aromatic substitution? 0 Br $03H N02 I ? b. Which of the following would be the most acidic? 0H 0H 0H 0H 0H “f: (3 CL CL CH3 ON ON c. Which of the following esters would not give a stable self-Claisen condensation product? 0 (M i ° o 05: H30 0Et “achEt d. Which of the following carboxylic acid derivatives would be the most reactive towards nucleophilic attack? 0 O o o 0 0 ,CH3 '1‘ Q/lOH OCHZCH3 NH2 0% CH3 e. Which of the following compounds would undergo decarboxylation upon mild heating? 0 O o o O O 0 CE OH HO O O O f. Which of the following compounds is aromatic? NAME last, first 810# 4. (16 points) Complete the following reactions by providing the appropriate starting material, reagent(s), or major product(s). O HCI H QTZNCHZCW + H20 col-+3 + HaNCHJLCH; CH3 on H: Kiowa-IQ oft 6)” I + CH30H -—-—* K \Owg 0 0 b + CH30H2NH2 catalyticH+ 4 i=NCHLCH3 b + (CHaCHflzNH catalytic H+ < / —- NéJ-l L043 1 0 B 1. (CH3)ZCuLi Q 2. H30+ E lCHa \ I OH 9. mam-berm2 l. KmMo‘r 7-- CH-s NHL‘ Dac— 4 5. (10 points) Jason, a student taking CHEM2212 for the third time, is attempting to prepare a13- hydroxy ketone using the aldol reaction. Jason had hoped to react propanal with 2- ethylcyclohexanone to obtain the desired product. When he carried out the reaction, Jason was surprised to find that he actually formed a mixture of 3 compounds, including his desired product. 0 OHO O NaOH \A + H H20, 5°C a. Draw the structures of the other two compounds formed in this reaction. b. Help Jason out by describing a synthetic method that would only give the desired product. NAME last, first 810# 6. (10 points) Write on the arrows the best reagents to accomplish the following transformations. Full credit will be awarded for the most efficient transformations. 5. scam.L m cit-4301+J H" 2.229,.thx O OO 6 7. (20 points) For the following problems, provide a synthesis of the indicated compound from the starting material provided. You may use any other necessary reagents. Organic reagents that you use in your synthesis (things that end up in your final product) must have <7 carbon atoms. Your s nthesis should rovide the desired roduct as the ma'or roduct in each step. 6 7. (20 points) For the following problems, provide a synthesis of the indicated compound from the starting material provided. You may use any other necessary reagents. Organic reagents that you use in your synthesis (things that end up in your final product) must have <7 carbon atoms. Your 3 nthesis should rovide the desired roduct as the ma'or roduct in each m- mu LT! T'LE © PRTHW MS wk. H NAME last, first 810# 8. (16 points) Starting from cyclohexene, design a synthesis using a Dieckmann cyclization (an intramolecular Claisen condensation) to synthesize cyclopentanone. Show all reagents and intermediate structures. (Hint: The rings are different sizes. So, you must open the cyclohexene ring to resize down to a five-membered cyclopentanone ring.) several steps 0 . ——-—-—I'- 8 9. (12 points) Using the curved arrow formalism, provide a detailed and stepwise mechanism for the following synthetic transformation. 1) NaOEt I Wcoza 2) H30+ 10. (10 points) The following IHNMR was obtained from the product formed upon reaction of diethylmalonate, NaOEt/EtOH, and a seven-carbon organohalogen. IR: 1710 cm"1 Intensity 10 9 a 7 6 5 4 3 2 1 0 ppm Chemical shift (a) a. Draw the structure of the product that gives the above lHNMR. b. Draw the structure of the 7-carbon organohalogen starting compound. 9 ll. Bonus (8 points). For the following transformation, provide a synthesis of the indicated compound from the starting material provided. You may use any other necessary reagents. Your 5 nthesis should rovide the desired roduct as the wafer roduct in each ste . ...
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Chem final exam - NAME 810# first last, CHEMISTRY 2212...

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