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Exam 1 Green

by: Andrew Winiarski

Exam 1 Green CEM 252

Andrew Winiarski

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Exam 1 from Spring 2016. Green Version. With Key
Organic Chemistry 2
Dr. Rathke
75 ?




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This 12 page Bundle was uploaded by Andrew Winiarski on Tuesday May 3, 2016. The Bundle belongs to CEM 252 at Michigan State University taught by Dr. Rathke in Fall. Since its upload, it has received 30 views. For similar materials see Organic Chemistry 2 in Chemistry at Michigan State University.


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Date Created: 05/03/16
Copyright  2016,  Professor  Michael  Rathke.   No  part  of  this  Exam  may  be  reproduced  or  transmitted  without  written  permission.     (14 total points, 2 pts. each) 1. Draw the structure of the following compounds: (2 pts.) a) m-bromobenzoic acid (2 pts.) b) o-methylaniline (2 pts.) c) benzaldehyde (2 pts.) d) p-nitrophenol (2 pts.) e) 2-methyl-2,4-heptadiene 2. Give the structure of the diene and the dienophile to complete the following Diels-Alder Reaction: (2 pts.) (2 pts.) O + O Diene Dienophile Copyright  2016,  Professor  Michael  Rathke.   No  part  of  this  Exam  may  be  reproduced  or  transmitted  without  written  permission.     (7 total points, 1 pt. each) 3. HBr a) For the above reaction, draw the two major resonance structures of the carbocation intermediate: (1 pt.) (1 pt.) b) Draw the structure of the 1,2 and the 1,4 addition products of the reaction: (1 pt.) (1 pt.) + 1,2 product 1,4 product c) Which of the above products (1,2 or 1,4) is more stable? (1 pt.) (1 pt.) d) Which of the above products (1,2 or 1,4) is formed faster? (1 pt.) e) Which of the above products (1,2 or 1,4) is the product under conditions of kinetic control? Copyright  2016,  Professor  Michael  Rathke.   No  part  of  this  Exam  may  be  reproduced  or  transmitted  without  written  permission.     (12 total points, 3 pts. ea.) 4. Purple compounds absorb visible light in the region of 555 nm while blue compounds absorb visible light in the region of 595 nm. One of the following compounds (A+B) is purple and the other is blue. Which one is blue (A or B) ? (CH ) N N(CH3 2 3 2 N(CH3 2 C C N(CH 3 2 N(CH 3 2 3 pts. A B Answer (A or B) 5. Which three of the following compounds (A-F) are expected to be aromatic according to Hückel’s Rule? H N H H CH CH2 HC O (+) (-) (-) HC N CH CH2 H HC CH A B D C E F 3 pts. 3 pts. 3 pts. , , Answers (A - F) Copyright  2016,  Professor  Michael  Rathke.   No  part  of  this  Exam  may  be  reproduced  or  transmitted  without  written  permission.     (12 total points, 3 pts. ea) 6. Give the symmetry (symmetric or antisymmetric) of the indicated molecular orbitals of the following conjugated systems: a) b) 3 pts. 3 pts. HOMO of the excited state LUMO of the excited state 7. Will the stereochemistry of the methyl groups be cis or trans in the product of the following electrocyclic reaction? H H H H (Wavy lines mean stereochemistry unspecified) C C CH H H CH 3 3 CH CH3 3 3 pts. answer 8. Will the following cycloaddition occur thermally (Δ) or photochemically (hυ)? CH3 CH 3 + CH CH 3 3 3 pts. answer (Δ or hυ) Copyright  2016,  Professor  Michael  Rathke.   No  part  of  this  Exam  may  be  reproduced  or  transmitted  without  written  permission.     (33 total points, 3 pts. ea) 9. Draw the structure of the major organic product(s): a) (3 pts.) OCH 3 (3 pts.) Cl2 + AlCl 3 b) CH 3 (3 pts.) KMnO 4 (excess) CH 2H 3 c) NO 2 (3 pts.) HNO 3 H 2O ,4 d) Br (3 pts.) (3 pts.) CH 3l + AlCl3 e) (3 pts.) (3 pts.) CH 2H 3 Br 2 + FeBr 3 f) (3 pts.) (3 pts.) CH(CH )3 2 AlCl3 + Cl C O g) NO 2 (3 pts.) Zn HCl CH 3 Copyright  2016,  Professor  Michael  Rathke.   No  part  of  this  Exam  may  be  reproduced  or  transmitted  without  written  permission.     (22 total points) 10. Draw the structure of the intermediate and the major organic product of the following reactions: a) (3 pts.) (3 pts.) CH 3 AlCl3 + CH 3 Cl CH 3 A Carbocation Electrophilic Addition Product (with more than 4 carbons) (3 pts.) b) (3 pts.) CH 2H 3 NBS A Carbon Radical Product c) . (3 pts.) (3 pts.) Cl NaC N NO 2 A Carbanion Nucleophilic Substitution Product 11. Outline the steps to complete the following synthesis: SO 3 CO 2 Make: From: and any other desired reagents (4 pts.)


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