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4 Questions on Organic Chemistry I with Answers - Exam 2 | CHEM 231, Exams of Organic Chemistry

Material Type: Exam; Class: Organic Chemistry I; Subject: Chemistry; University: University of Maryland; Term: Fall 2002;

Typology: Exams

Pre 2010

Uploaded on 05/09/2008

koofers-user-e4o
koofers-user-e4o 🇺🇸

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Download 4 Questions on Organic Chemistry I with Answers - Exam 2 | CHEM 231 and more Exams Organic Chemistry in PDF only on Docsity! Chemistry 233 Exam 2 Nov 7,2002 Dr. B. B. Jarvis Name _______ Section* & TA There are 6 pages to this exam, including the cover page. Please be sure you have all five pages. There are 4 questions and 160 points on this exam. 1 2 3 4 Total Read each question carsfully. 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. 1. (96 pts) Multiple choice. Questions have only one answer. a) Identify the compound that would be the MAJOR product in the following reaction Answer_____ CH KOH Br' "CH3 EtOH CH, CH B CH3 b) Hydroxylations of :he cis- and trans-isomers of 2-butene with OsO4 lead to different diastereomeric 2,3-butanediols. Although as isolated from this reaction, neither compound exhibits optical activity, one of the products can be resolved into a pair of optically active 2,3-butanediols. Which statement below is correct as applied to the above? Answer ____ A: trans-2-Butene reacts to give a meso diasteomer that can be resolved into a pair of enantiomers, while the cis-isomer gives a resolvable racemic diastereomer B: cis-2-Butene reacts to give a meso diasteomer that can be resolved into a pair of enantiomers, while the trans-isomer gives a resolvable racemic diastereomer C: Only one of the 2-butenes reacts stereospecifically and thus is able to give a product that can be resolved into its enantiomers. D: The trans-isomer reacts to give a racemic diastereomer than can be resolved into a pair of enantiomers. c) Identify the group with the LOWEST prioity in the Cahn-lngold-Prelog system Answer_____ O O=CH CH:==: CH2 C^p.,, Q^sfvj A B C D d) Treatment of a hydrocarbon C7H 12 with ozone followed by Zn / \-\3O* gives compound Y. The original hydrocarbon C7H 12 has which structure? Answer -CH2CH3 A 2. (20 pts) Indicate whether the statements below are true (T) or false (F) a) Acid-base equilibria favor the weaker acids & bases b) Free radical substitutions (RH to RX) are typically more selective for brominations than they are for chlorinations c) Cyclohexane rings always prefer the chair conformation d) In chemical reactions, the more stable product is always formed more rapidly than the less stable product. e) Sodium hydroxide is a stronger base that typical Grignard reagents 3. (20 pts) Provide a detailed reaction mechanism for one of the reactions below. OMIT ONE -CROSS IT OUT. Pay CAREFUL ATTENTION to stereochemistry. a. H CH, Br2 EtOH HBr + (pCH2CH3 Ph9-CHBrCH3 CH3 One diastereomer & it is racemic b. Br, hV + HBr 4. (24 pts) Carry out 4 of the following transformations. OMIT ONE -cross it out. More than one step may be involved. You may use any inorganic reagents or organic reagents with 2 or fewer C's. a. c. (Mixture of cis/trans isomers)
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