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Reference Guide for Medicinal & Organic Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers REFERENCE GUIDE FOR MEDICINAL & ORGANIC CHEMISTRY QUESTIONS & ANSWERS 2009-2010 Manan H. Shroff www.pharmacyexam.com 1 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers REFERENCE GUIDE FOR MEDICINAL & ORGANIC CHEMISTRY QUESTIONS & ANSWERS 2009-2010 www.pharmacyexam.com 2 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers This reference guide is not intended as a substitute for the advice of a physician. Students or readers must consult their physician about any existing problem. Do not use any information in this reference guide for any kind of self-treatment. Do not administer any dose of mentioned drugs in this reference guide without consulting your physician. This is only a review guide for preparation for the Foreign Pharmacy Licensing board exam. The author of this reference guide is not responsible for any kind of misinterpreted, incorrect or misleading information or any typographical errors in this guide. Any doubtful or questionable answers should be checked in other available reference sources. All rights reserved. No part of this guide may be reproduced or transmitted in any form or by any means, electroni- cally photocopied, recorded or otherwise , without prior written permission of the publisher. RXEXAM is a registered trademark of Pharmacy Exam of Krishna Publication Inc. Any unauthorized use of this trademark will be considered a violation of law. NAPLEX and FPGEE are federally registered trademarks owned by the National Associa- tion of Boards of Pharmacy (NABP) and this reference guide is in no way authorized or spon- sored by NABP. www.pharmacyexam.com 3 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers REFERENCE GUIDE FOR MEDICINAL & ORGANIC CHEMISTRY QUESTIONS & ANSWERS 2009-2010 Manan H. Shroff www.pharmacyexam.com 4 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers Preface: Reference Guide For Medicinal and Organic Chemistry - Questions and Answers” is specifically written for students preparing for the FPGEE and Canadian Evaluating Exams. It has 500 questions with answers and complete explanations. Recently, the exam puts more emphasis on graph- and structure-based questions, therefore an effort was made to include all of these topics in a review guide. Each answer is explained thoroughly to refresh your memory on specific topics. Please do not go through only the questions and answers. Try to understand and learn the answer’s explana- tions. It is the best way to get the most out of this review guide. I hope my efforts will help you to pass your key exam. I wish you the very best of luck, and any questions or comments are always welcome. Manan Shroff www.pharmacyexam.com 5 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers TABLE OF CONTENTS SECTION-I QUESTIONS 7 SECTION-II ANSWERS 87 www.pharmacyexam.com 6 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers 1. Which of the following is incorrectly pre- 3. Which of the following is falsely pre- sented? sented? F2 a. Cl Be Cl a. CH 4 CH3F + HF 1800 Cl2 b. F CH4 CH Cl + HCl b. B F 3 F Br2 0 120 c. CH 4 CH3Br + HBr .. c. H O H I2 d. CH 4 CH3I + HI 1800 H 4. Which of the following statements is true about the following chart? C H d. H H 109.50 2. Which of the following molecules has the largest dipole? a. H F Cl b. C Cl Cl Cl a. The temperature is a measure of the average kinetic energy. Cl b. Kinetic energy of the moving molecules is not the source of the energy needed for c. C H reaction. H c. The number of molecules with a par- H ticular kinetic energy is greatest for an energy near the average and decreases as the energy d. O becomes larger or smaller than the average. H H d. The size and weight of the particles are characteristic of each reaction and cannot be changed. www.pharmacyexam.com 7 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers 5. Which of the following is true about the c. Z-X = exothermic energy graphic presentation? d. X + Y = exothermic energy 8. What is the mass number of lithium? a. 3 b. 4 c. 7 d. 1 a. It is an endothermic reaction. b. The b-portion is called activation energy. 9. Which of the following is an isotope of c. The a-portion is the energy given off. hydrogen? d. It is an exothermic reaction. 6. On a following graphical presentation, identify the activation energy for a reaction. 10. Which of the following statements are TRUE about the following graphical presenta- tion? a. W b. X c. Y d. Z 7. From the graph of question 6, one can say that: a. Z = exothermic energy b. Z-Y = exothermic energy www.pharmacyexam.com 8 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers I. The high boiling point of water is due 12. What is the boiling point of CCl4 ? to its ability to form strong H-bonding. II. The H-bond formation is the strongest in H2Te. III. The increase of the boiling point of a compound is directly proportional to its molecular mass. a. I only b. I and II only c. II and III only d. All 11. Which of the following statements are TRUE about the relationship between kinetic a. 760 o energy and number of molecules? b. 100 o c. 20 o d. 80 o 13. Which of the following pentane struc- tures has the lowest boiling point? a. CH3 CH2 CH2 CH2 CH3 b. CH3 CH2 CH CH3 CH3 CH3 I. As the temperature of a gas increases, c. CH C CH its kinetic energy is increased. 3 3 CH II. Temperature increases a measure of the 3 average kinetic energy of the particles. d. CH3 CH CH2 CH3 III. The average kinetic energy of molecules is found at the peak of the curve. CH3 a. I only b. I and II only c. II and III only d. All www.pharmacyexam.com 9 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers 14. Which of the following arrangements lists the compounds below in the order of decreasing the bond dissociation energy (high- energy first, least-energy last)? 3. 1. CH4 2. CH3CH3 3. CH3CH2CH3 4. CH3 4. CH3 C CH3 CH3 a. 1 and 3 a. 1 > 2 > 3 > 4 b. 2 and 4 b. 4 > 3 > 1 > 2 c. 3 and 2 c. 2 > 4 > 3 > 1 d. 4 only d. 1 > 4 > 3 > 2 16. Which of the following compounds does 15. Which of the following compounds NOT contain a chiral carbon? represents a pair of diastereomers? H 1. Cl I SO3H 1. (Chloroiodomethanesulfonic acid) H 2. CH3 CH3 Cl Isopropyl chloride 2. H 3. CH3 COOH OH (Lactic acid) www.pharmacyexam.com 10 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers H 19. How many enantiomers are possible for 2,3-Dichloropentane? 4. CH3 C2H5 CH3 CH CH CH2 CH3 Cl Cl Cl (sec-Butyl chloride) 2,3-Dichloropentane a. 1 b. 2 a. 1 c. 3 b. 3 d. 4 c. 4 d. 5 17. What is the complete name for the opti- cally active compound listed below? 20. Which of the following is (R)-3- hexanol? a. (+)-Bromochloroiodomethane b. (S)-Bromochloroiodomethane c. (R)-Bromochloroiodomethane d. (RS)-Bromochloroiodomethane 18. In the following compound what would be the correct configuration sequence of atoms attached to the chiral carbon? H C C H CH3CH 2 5 CH3 Cl 3-chloro-2-methylpentane a. fig-1 b. fig-2 a. Ethyl > Cl > Isopropyl > H c. fig-3 b. Cl > Ethyl > H > Isopropyl d. fig-4 c. Cl > Isopropyl > Ethyl > H d. Isopropyl > Cl > Ethyl > H www.pharmacyexam.com 11 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers 21. Which two fischer formulas represent a 23. Which of the following compounds pair of enantiomers? represents a pair of enantiomers? a. X and Y b. X and Q c. Z and Y d. Z and R 24. Pure (R)-2-pentanol has a specific rota- tion of -10.50 degrees. You have purified a sample that has a calculated specific rotation of a. I and IV -2.625 degrees. What can you conclude about b. II and III this sample? c. III and I d. II and IV a. The sample has completely racemized b. 75% of the sample has rearranged into 22. Which of the following compounds is a meso-isomer (S)-4-bromo-1-methylcyclohexene? c. 50% of the sample has racemized d. 75% of the sample has racemized 25. Which of the following is classified as a meso- compound? a. I b. II c. III d. IV www.pharmacyexam.com 12 Reference Guide for Medicinal and Organic Chemistry Krisman - Questions and Answers 28. Which of the following C8H16 isomers is thermodynamically most stable? a. i b. ii c. iii d. iv a. R b. S 26. How many stereoisomers of c. T (CH3)2CHCH=CHCH2CH(OH)CH2Br are pos- d. U sible? 29. How many stereoisomers are possible a. 5 for the following compound? b. 4 c. 2 d. 0 27. A C7H14O optically active alcohol (3,3- Dimethylcyclopentanol) is oxidized by Jones’ reagent to an optically inactive (achiral) ketone. What is the correct structural formula for this compound? a. 2 b. 4 c. 8 d. 10 30. Which of the following compounds has the highest boiling point? a.
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