Academic Integrity - Exam 3 for Principles of Organic Chemistry I | CHEM 237, Exams of Organic Chemistry

Download Academic Integrity - Exam 3 for Principles of Organic Chemistry I | CHEM 237 and more Exams Organic Chemistry in PDF only on Docsity! Chemistry 237 \ » ^Exam3 Dec. 3,2003 Dr. B. B. Jarvis \^^^ NAME___________ Section No. _======^===== There are 7 pages to this exam, including the cover page. Please be sure you have all seven pages. There are 5 questions (160 points) + Extra Credit and on this exam. I II . III IV V EC Total Read each question carefully. All answers must be entered on the exam sheets. You will not need a calculator or any other materials other than writing implements and your model set. Please be sure that all other materials are out of reach and sight. Please put your name and lab section and TA name on each page of the exam. GOOD LUCK!!! ACADEMIC INTEGRITY: Violations of the Code of Academic Integrity will not be tolerated. Suspected cases will be reported immediately to the appropriate authorities. All work submitted for grading (quizzes, exams, lab reports) must be the original work of the student whose name appears on the work. Group or pair projects, approved by the professor, must have all participants names on the work with the indication that students were instructed to work in pairs or groups. The same work cannot be submitted for credit in two different courses or from semester to semester in the same course (e.g., repeated lab exercises) without the written permission of all instructors involved. V (10 pts) Carry out ONE of the following syntheses. OMIT ONE -cross it out. You may use any inorganic reagents and any alkyl halide with 3 or fewer carbon atoms. a) Don't even think of using CH3CHC1CN + AIC13 -You'll get ZERO for the question b) o Extra Credit (20 pts). Give the approximate pKa's of the following compounds: HCI Ammonia Ethene Acetylene._ Phenol (30 pts). Complete the following roadmap question. OH I. (36 pts). Give brief explanations for the following. a) Cyclobutadiene is an exceedingly unstable compound. However, the cyclobutenyl dication is a surprisingly stabe cation for one that has two positive charges on carbon atoms. Cyclobutenyl Dication g) The one compound below that will be able to form a Grignard reagent. Br Br Br Br NH5 OCH3 h) The one diene that will not undergo a Diel-Alder reaction OCHq i) The BEST leaving group in an SN 1 or SN2 reaction CH3S HoO Br 9 < CH3C-O j) An anti-aromatic compound. Assume that the rings are planar. H O 0r\ Sulfathiazole k) Which statement is TRUE about sulfathiazole? /_ 1. Sulfathiazole is non-aromatic 2. Sulfathiazole is aromatic 3. Sulfathiazole is anti-aromatic 4. Sulfathiazole is non-planar 5. Sulfathiazole will be a very reactive diene in the Diels-Alder reaction 1. (60 pts) Answer NINE (9) of the following questions. OMIT TWO -cross them out. There is only one correct answer for each question. Circle the correct answer. a) LEAST reactive in an SN2 reaction. Cl ^sX OTs Br b) MOST reactive in an SN 1 reaction. -Cl OTs c) MOST reactive base for an E2 elimination. CH3CH2COCf Na+ / EtOH KOH/EtOH t-BuO' Na+ / r-BuOH ?-BuO~ Na+ / DMSO d) BEST solvent for an SN 1 reaction. Et?O i-PrOH DMF HCOOH (40%) -H2O (60%) Acetone e) In reactions where the major product (MP) is both the kinetic and the thermodynamic product, the following is true. 1. The MP has both a higher energy and a higher transition state leading to it. 2. The MP has both a lower energy and a lower transition state leading to it. 3. The MP has a lower energy but a higher transition state leading to it. 4. The MP has a higher energy but a lower transition state leading to it. 5. None of the above f) An optically active compound that will likely give a mixture of CHIRAL products upon treatment with NBS/CC14 with peroxides or light. CH 3 tCH2 /—\ ^X, ^-^ / ^-^ H HPCH3 CH(CH2 )2