Final - Practice B - Organic Chemistry: Chem 38 Practice...

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Organic Chemistry: Chem 38 Practice Exam 4 B There are 28 questions on this exam including one spectral problem. Check that you have done all of the problems and filled in the first 28 bubbles on the scantron. The number of points per question are clearly labeled in the text. The maximum score on the exam is 100 points. Instructions Answer sheet 1) You need to clearly write your name and fill in your student number, section number and test form on the scantron. 2) White = test form A Yellow = test form B 3) Section one = 12:20 pm class Section two = 3:35 pm class 4) Use a #2 pencil Exam policy 1) Molecular models are allowed, calculators are not allowed. 2) The back of the test can be used for scratch paper. 3) Relevant tables, including the periodic table, are attached the end of this exam. 4) You cannot take a copy of the exam with you. You may copy your answers onto the provided page. The answer key will be posted on the web after the exam. Hints 1) As you read the question, underline or circle key words to highlight them for yourself. 2) Some questions have more than one acceptable answer. Pick the best one for full credit. Partial or full credit will be given for other acceptable answers. 3) There is no penalty for guessing. 1
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1 . (4 pts) The first transition state in the overall exergonic addition of HBr to propene resembles the intermediate (carbocation). Chose the best phrase to complete the following statement: The second transition state (for addition of Br to the carbocation) . ...... a) resembles the final product b) resembles the 2-propyl cation c) resembles propene d) has all carbons almost entirely sp 3 hybridized e) has much higher energy than the first transition state f) has both carbons of the former π system sp 2 hybridized 2 . (4 pts) The alternative reaction pathways for radical chain reactions of Br 2 with ethane may be represented as follows: CH 3 CH 3 (1) + Br 2 CH 3 CH 2 HBr 2 + CH 3 CH 3 (2) + CH 3 2 Which statement is correct? a) reaction (1) is more likely because it is more endothermic b) reaction (2) is more likely because it is more endothermic c) reaction (1) is more likely because it is more exothermic d) reaction (2) is more likely because it is more exothermic e) reactions (1) and (2) are equally likely because they have almost identical H rxn f) both reactions are unlikely, because they are too much uphill in energy 2
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3 . (4 pts) What is the product of the following reaction? CH 3 CH 2 CH 2 CC C H 3 H 2 O, H 2 SO 4 HgSO 4 b) CH 3 CH 2 CH 2 CH 2 CH 2 CH 2 OH c) CH 3 2 2 CCH 2 CH 3 O d) 3 2 2 2 3 O e) c and d a) 3 2 2 CHCH 2 3 4. (4 pts) The main reasons for the following rearrangement are: Cl CH 3 HCl a) the initially formed carbocation is secondary, and it rearranges to the more stable tertiary one by shift of an alkyl group b) the reaction converts one tertiary carbocation into another to relieve torsional strain c) the tertiary chloride is much more stable than a secondary one, because of hyperconjugation d) this is a radical chain reaction, controlled by relative bond strengths 3
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5 . (4 pts) What is the main product of the following reaction?
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This note was uploaded on 06/16/2009 for the course CHEM 210 taught by Professor Maslak,przemyslaw during the Fall '08 term at Pennsylvania State University, University Park.

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Final - Practice B - Organic Chemistry: Chem 38 Practice...

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