Test Bank For Organic Chemistry: Structure and Function, 8th Edition

Name: __________________________ Date: _____________ 1. The correct name of the following molecule would be: A) B) C) D) E) 2-ethyl-3,3-dimethylheptane 6-ethyl-5,5-dimethylheptane 3,4,4-trimethyloctane 2-butyl-3-methylpentane 2-sec-butyl-2-methylhexane 2. What is the name given to the Newman projection of the butane conformation shown here? CH3 CH3 H H H H A) B) C) D) E) anti gauche staggered eclipsed skewed 3. At room temperature, the various conformations of butane A) do not interconvert with only the anti form present. B) do not interconvert, but all forms are present. C) interconvert slowly. D) interconvert rapidly. E) There is no way to determine if interconversion occurs. Page 1 4. What statement is true of the following energy diagram? SM prod 2 prod 1 A) B) C) D) E) For irreversible reactions, product 1 will dominate. For reversible reactions, product 2 will dominate at equilibrium. For reversible reactions, equal amounts of 1 and 2 will be formed. For irreversible reactions, equal amounts of 1 and 2 will be formed. None of the above are true. 5. What would be the correct name of the following? CH3 CH2 CH2 CH CH3 CH3 A) B) C) D) E) CH2 CH CH2 CH3 3-(sec-pentyl)pentane 5-ethyl-4-methylheptane 3-(sec-butyl)hexane 3-ethyl-4-methylheptane 3-ethyl-4-propylpentane 6. The following Newman projection corresponds to which molecule? H CH2CH3 H H CH3CH2 H A) B) C) D) E) pentane butane 3-ethylbutane hexane 3-methylpentane Page 2 7. Rotation around the carbon-carbon bond of the molecule depicted by the following Newman projection requires how much energy? H H H H H H A) B) C) D) E) 0 kcal/mol 3 kcal/mol 6 kcal/mol 9 kcal/mol 15 kcal/mol 8. What is the correct IUPAC name for the following molecule? A) B) C) D) E) 1,1,1,4-tetramethylhexane 4-ethyl-1,1,1-trimethylpentane 5-ethyl-2,2-dimethylhexane 3,6,6,6-tetramethylhexane 2,2,5-trimethylheptane 9. The following represents what functional group? R A) B) C) D) E) O R ester ether alcohol thiol ketone Page 3 10. The following represents what functional group? O R A) B) C) D) E) H alcohol aldehyde carboxylic acid amide ketone 11. The following represents what functional group? R C A) B) C) D) E) N amide thiol ketone nitrile amine 12. What is the correct structure for tert-butyl bromide? A) Br B) Br C) Br D) Br E) Br Page 4 13. The following Newman projection represents which molecule? CH3 H3CH2CH2C CH2CH3 H CH2CH2CH3 CH3 A) B) CH3 CH3 C) D) E) Page 5 14. Name the following functional group: O R A) B) C) D) E) O O R ester ketone alcohol carboxylic acid anhydride 15. Which isomer of C7H16 shown would have the highest boiling point? A) B) C) D) E) 16. Which of the following contains the isobutyl group? A) (CH3)2CHCH2Cl B) (CH3)3CCl C) CH3CH2CH(CH3)Cl D) CH3CH2CH2CH2Cl E) None of the above. Page 6 17. Which of the following contains the sec-butyl group? A) (CH3)2CHCH2Cl B) (CH3)3CCl C) CH3CH2CH(CH3)Cl D) CH3CH2CH2CH2Cl E) None of the above. 18. How would the following molecule be properly named? CH3 CH3 CH CH3CH2 CH HC CH2CH2CH3 CH2 CH3 A) B) C) D) E) 3-ethyl-2-methyl-4-propylhexane 3,4-diethyl-2-methylheptane 4-ethyl-3-isopropylheptane 3-isopropyl-4-propylhexane None of the above. 19. The IUPAC name for [(CH3)3C]2CHCH3 is: A) 1,1-di-tert-butylethane B) 3-tert-butyl-2,2-dimethylbutane C) 2,2,3,4,4-pentamethylpentane D) 2,4,4-trimethylheptane E) None of the above. 20. What is the smallest alkane that is liquid at room temperature? A) propane B) butane C) pentane D) hexane E) All are liquids. Page 7 21. All steroids are derivatives of the ring system shown. How many tertiary hydrogens are in this ring system? A) B) C) D) E) none 2 4 5 6 22. What is the correct IUPAC name for the following molecule: A) B) C) D) E) 2-ethyl-2,6-dimethylheptane 1,1,5,5-tetramethylhexane 1,1,5,5-tetramethylheptane 2,6,6-trimethyloctane 4,4-dimethyl-1-isopropylhexane 23. What is the name given to the Newman projection of the butane conformation shown here? CH3 H H H H CH3 A) B) C) D) E) eclipsed gauche staggered anti skewed Page 8 24. Calculate Go for the following reaction at 25 oC and S=0 A) B) C) D) E) –10 kcal/mol 10 kcal/mol 34 kcal/mol –34 kcal/mol None of the above. 25. Which of the following has the highest pKa? A) HI B) NH3 C) HNO3 D) CH3COOH E) H2SO4 26. The common name for 1-methylpropyl is: A) Isopropyl B) Isobutyl C) sec-Butyl D) tert-Butyl E) None of the above. Page 9 27. What is the correct Newman projection for the following molecule? H3 C H3CH2 C Cl Br A) Cl (CH2)2CH3 CH3 Br CH2 CH3 CH3 B) Cl (CH2)2CH3 CH3 H3CH2 C Br CH3 C) Cl CH2 CH3 CH3 H3CH2 C Br CH3 D) Cl (CH2)2CH3 CH3 Br CH2 CH3 H E) None of the above. Page 10 28. Which of the following molecules contain both an alcohol and an aldehyde functional group? A) O O B) OH H O C) O NH2 HO D) O OH O E) CO2 H H N O Page 11 29. Consider the potential energy diagram for rotation about the C2–C3 bond in pentane. The position marked “A” most likely corresponds to which of the following Newman projections? A) H H CH2 CH2CH3 H H CH3 B) CH2 CH3 H H H H CH3 C) H CH3 H H H CH2 CH3 D) H H CH2 CH3 H CH3 H E) Page 12 H CH3 CH3 H H H 30. What is the correct IUPAC name for the following molecule? A) B) C) D) E) 6-propyl-5,7,8-trimethyldecane 5,7,8-trimethyl-6-propyldecane 3,4,6-trimethyl-5-propyldecane 5-propyl-3,4,6-trimethyldecane None of the above. 31. Which of the following is not considered a Lewis acid? A) H B) CH3OH C) AlCl3 D) CH3 H3 C C CH3 E) BF3 Page 13 32. Which of the following is considered to be a nucleophile? A) CH3Cl B) CH3CH2I C) NH3 D) E) H3 C C H CH3 33. Which of the following reactions has a S = 0? A) Br + Br2 Br B) CH3CH2Cl + NaOH → CH2=CH2 + H2O + NaCl C) + Br hv Br2 + HBr D) H H E) • CH3 CH3 I CH3 H3C CH3 + HI None of the above. 34. How many quaternary carbons are in the following molecule? A) B) C) D) E) 0 1 2 3 4 Page 14 35. How many ester functional groups are in the potent anticancer compound Taxol? O CH3 O O O O OH N H O OH O O O Taxol A) B) C) D) E) 0 1 2 3 4 36. Arrange these acids in the order of increasing acidity. HCl A) B) C) D) E) HBr HI HF HBr, HI, HF, HCl HF, HCl, HBr, HI HF, HBr, HCl, HI HI, HCl, HBr, HF HI, HBr, HCl, HF 37. Arrange these acids in the order of increasing acidity. CH4 H2O A) B) C) D) E) CH4, H2O, HF, NH3 HF, H2O, CH4, NH3 HF, H2O, NH3, CH4, CH4, NH3, H2O, HF, NH3, CH4, H2O, HF, HF NH3 Page 15 38. What is the correct IUPAC name for the following molecule? A) B) C) D) E) 1-ethyl-2-methylhexane 2-ethyl-1-methylcycloheptane 4-ethyl-5-methylcyclohexane 1-ethyl-2-methylcyclohexane 1-methyloctane 39. Guanacastepene is a natural product that was recently isolated and shown to be a potent antibiotic. How many different functional groups does this structure possess? A) B) C) D) E) 1 2 3 4 5 Page 16 Answer Key 1. C 2. B 3. D 4. E 5. D 6. D 7. B 8. E 9. B 10. B 11. D 12. B 13. A 14. E 15. A 16. A 17. C 18. B 19. C 20. C 21. E 22. D 23. D 24. A 25. B 26. C 27. A 28. B 29. B 30. C 31. B 32. C 33. C 34. B 35. D 36. B 37. D 38. D 39. E Page 17