Organic Chemistry : ACS Exams_ACS Organic Final Practice Exam. 70 Questions

Organic Chemistry : ACS Exams_ACS Organic Final Practice Exam What is the correct Lewis structure for PH3? A. I B. II C. III D. IV E. V 2. Rank the following compounds in decreasing order of b oiling point. A. III I IV II B. II IV III I C. III I II IV D. IV II I III E. I III II IV 3. Which of the following compounds have +1 as a formal charge on an oxygen atom? A. I B. II C. III D. IV E. Both I and IV 4. What is the relationship between the following two compounds? A. constitutional isomers B. identical compounds C. completely different and not constitutional isomers 5. Which of the following is a Newman projection for the following compound as viewed down the indicated bond in the conformation shown? A. I B. II C. III D. IV Page 2 of 14 6. Which of the following is/are the most significant resonance structure(s)? A. I B. II C. III D. I and III E. all of these 7. Which of the following is a correct resonance structure for compound A? A. I B. II C. III D. IV E. none of these 8. Which of the following is the correct bond-line structure for (CH3)2CHCH2CH3? A. I B. II C. III D. IV E. None of these 9. Which of the following compounds have trigonal planar electron geometry? A. I, II and III B. I, II, IV and V C. III and IV and V D. II and III E. All of these 10. Which of the indicated carbon atoms have sp2 hybridization state in the following compound? A. I and II B. III and IV C. II and III D. I and III 11. Which of the following compounds is most acidic? A. I B. II C. III D. IV E. All of these Page 3 of 14 12. Which of the following is a gauche conformation for butane? A. I B. II C. III D. IV 13. Which of the following is the most stable isomer? A. I B. II C. III D. IV 14. Which of the indicated protons is most acidic? A. I B. II C. III D. IV E. All of these 15. For the following acid-base reaction, predict which side of the equilibrium is favored. A. favor right side B. favor left side C. neither 16. For the following reaction, identify the Lewis acid. A. I B. II C. III D. Both I & III 17. Which of the following is the correct structure pentanol? for the compound (R)-2- A. I B. II C. III D. IV Page 4 of 14 18. What is the relationship of the following two structures? A. enantiomers B. diastereomers C. constitutional isomers D. identical 19. Consider the following SN2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of NaN3 is tripled? A. No effect B. It would double the rate C. It would triple the rate D. It would increase four times E. It would increase the rate six times 20. Which of the following choices is a diastereomer of the first structure shown? A. I B. II C. III D. IV 21. Rank the following from most to least stable. A. I II III B. III II I C. II III I D. II I III E. I III II 22. What set of reaction conditions would favor an SN1 reaction on 2-bromo-3- methylbutane? A. weak nucleophile in a protic solvent B. weak nucleophile in an aprotic solvent C. strong nucleophile in a protic solvent D. strong nucleophile in an aprotic solvent 23. What is the expected major product of the following reaction? A. I B. II C. III D. IV E. V Page 5 of 14 24. What substitution reaction mechanism is most likely for the following compound? A. SN1 B. SN2 C. Either SN1 or SN2 D. None of these 25. Which of the following is a correct Fischer projection of the following compound? A. I B. II C. III D. IV 26. What is the correct structure for (2S,5R)- 2-fluoro-5-methylnonane? A. I B. II C. III D. IV 27. Identify the expected major product of the following reaction.