TEST BANK For Organic Chemistry 10th Edition By Francis Carey || Verified All Chapters 2024 | Updated Version 2024 A+

TEST BANK For Organic Chemistry 10th Edition By Francis Carey || Verified All Chapters 2024 | Updated Version 2024 A+ 1. What is the ground state electron configuration of carbon? A. 1s2 2s2 2px1 B. 1s2 2s2 2px2 C. 1s2 2s2 2px12py1 D. 1s2 2s2 2px22py1 Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.01 Subtopic: Periodic table trends Topic: Structure and Bonding 2. Which of the following has (have) the same electron configuration as Ne? Na- Mg2+ O2- Mg + A. Na- and O2- B. Mg2+ and O2- C. Mg+ and O2- D. only Mg2+ Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.02 Subtopic: Periodic table trends Topic: Structure and Bonding 3. What is the letter designation given to dumbbell shaped orbitals like the one depicted below? A. s B. p C. d D. f Bloom's Level: 1. Remember Chapter: 01 Difficulty: Easy Gradable: automatic Section: 01.01 Subtopic: Atomic orbitals Topic: Molecular Shape 4. Which of the following atoms has vacant d orbitals that permit it to accommodate more than eight electrons in its valence shell? A. N B. C C. Ne D. S Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 01 Difficulty: Easy Gradable: automatic Section: 01.08 Subtopic: Octet rule exceptions Topic: Structure and Bonding 5. Predict which bond is the most polar in ethanol, CH3CH2OH? A. C-C B. C-H C. C-O D. O-H Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.04 Subtopic: Bond properties Subtopic: Types of bonds Topic: Structure and Bonding 6. Which one of the following is the conjugate base of NH3? A. NH4+ B. H + C. N3- D. NH2 - Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.12 Subtopic: Acid/Base definitions Topic: Acids and Bases 7. What can be said about the polarity of the C=O bond? A. C and O have the same electronegativity; the bond is nonpolar B. the C=O bond is polar; the O atom bears a partial negative charge C. the C=O bond is nonpolar; the C atom bears a partial positive charge D. the C=O bond is polar; the C atom bears a partial negative charge Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.04 Subtopic: Bond properties Subtopic: Types of bonds Topic: Structure and Bonding 8. Identify the condensed formula of the following structure: A. (CH3)2CHCHClCH(CH3)2 B. CH3CH(CH3)CHClCH(CH3)2 C. (CH3)2CHCHClC(CH3)3 D. (CH3)3CCHClCH(CH3)3 Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Condensed formula Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 9. What is the chemical formula of the following carbon skeleton diagram? A. C8H14 B. C8H16 C. C8H18 D. C8H20 Bloom's Level: 2. Understand Chapter: 01 Difficulty: Easy Gradable: automatic Section: 01.06 Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 10. How many hydrogen atoms are there on carbon atoms 1 and 2, respectively, in the structure below? A. 4, 1 B. 4, 0 C. 3, 1 D. 3, 0 Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 11. How many C3H8O constitutional isomers are possible? A. one B. two C. three D. four Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Constitutional isomers Topic: Drawing Organic Molecules 12. Which of the following best describes the relationship between the two structures? A. identical compounds B. resonance structures C. constitutional isomers D. different compounds with different constitutions Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 13. How many constitutional isomers of C4H9Br are possible? A. one B. two C. three D. four Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Constitutional isomers Topic: Drawing Organic Molecules 14. How many constitutional isomers of C3H6Cl2 are possible? A. three B. four C. five D. six Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Constitutional isomers Topic: Drawing Organic Molecules 15. What is the formal charge on the carbon atom? A. +1 B. 0 C. -1 D. -2 Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.05 Subtopic: Formal charges Topic: Structure and Bonding 16. Which of the following describes the relationship between the following two structures? A. identical structures B. resonance forms C. constitutional isomers D. different compounds with different compositions Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 17. Which of the following describes the relationship between the following two ions? A. identical structures B. resonance forms C. constitutional isomers D. different compounds with different compositions Bloom's Level: 2. Understand Chapter: 01 Difficulty: Easy Gradable: automatic Section: 01.07 Subtopic: Resonance Topic: Structure and Bonding 18. What is the formal charge on the oxygen atom in the structure below? A. -1 B. 0 C. +1 D. +2 Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.05 Subtopic: Formal charges Topic: Structure and Bonding 19. What is the formal charge on the nitrogen atom in the structure below? A. -1 B. 0 C. +1 D. +2 Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.05 Subtopic: Formal charges Topic: Structure and Bonding 20. The formal charges on the nitrogen and oxygen in the following structures are, respectively A. +1, -1 B. 0, -1 C. +1, 0 D. 0, 0 Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.05 Subtopic: Formal charges Topic: Structure and Bonding 21. In which of the following compounds would you expect Cl to have a partial positive charge? A. HCl B. CCl4 C. NaCl D. HOCl Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.04 Subtopic: Bond properties Subtopic: Types of bonds Topic: Structure and Bonding 22. Based on the VSEPR model, which of the following species has (have) a trigonal planar geometry? I. BCl3 II. NH3 III. NO3¯ A. only I B. I and II C. I and III D. I, II, and III Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.09 Subtopic: VSEPR theory Topic: Molecular Shape 23. Based on VSEPR theory, which of the following species has (have) a trigonal pyramidal geometry? I. CO32- II. NH3 III. CH3+ A. only I B. only II C. I and II D. II and III Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.09 Subtopic: VSEPR theory Topic: Molecular Shape 24. Which of the following species has(have) a linear geometry? I. CO2 II. NO2 + III. NO2¯ A. only I B. only II C. I and II D. I, II, and III Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.09 Subtopic: VSEPR theory Topic: Molecular Shape 25. Which of the following molecules would you expect to have a dipole moment? I. CO2 II. HCN III. CHCl3 A. II and III B. only II C. only III D. I, II, and III Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.10 Subtopic: Dipole moments Subtopic: Polarity of molecules Topic: Molecular Shape 26. Which of the following molecules would you expect to have a dipole moment? I. CH2Cl2 II. CH3Cl III. CCl4 A. only I B. only II C. I and II D. I, II, and III Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.10 Subtopic: Dipole moments Subtopic: Polarity of molecules Topic: Molecular Shape 27. The H-C-H bond angles in ethylene, C2H4, are closest to A. 90°. B. 109.5°. C. 120°. D. 180°. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.09 Subtopic: Hybridization Topic: Molecular Shape 28. The C-C-C bond angle in propane, C3H8, is closest to A. 90°. B. 109.5°. C. 120°. D. 180°. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.09 Subtopic: Hybridization Topic: Molecular Shape 29. What are the formal charges of boron and nitrogen, respectively, in the following structure? A. -1 and +1 B. -1 and 0 C. 0 and +1 D. 0 and 0 Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.05 Subtopic: Formal charges Topic: Structure and Bonding 30. Which one of the following is isoelectronic with CO2? A. NO2¯ B. NO2+ C. NO2 D. O3 Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.10 Subtopic: Dipole moments Subtopic: Polarity of molecules Subtopic: VSEPR theory Topic: Molecular Shape 31. In which of the following does hydrogen have a partial negative charge based on electronegativity? A. BH3 B. CH4 C. NH3 D. H2O Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.04 Subtopic: Bond properties Subtopic: Types of bonds Topic: Structure and Bonding 32. Which of the following species have a zero formal charge on its carbon atom? A. I and II B. II and IV C. III and IV D. I, II, and III Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.05 Subtopic: Formal charges Topic: Structure and Bonding 33. Which one of the following species is formed when diazomethane loses a nitrogen molecule? diazomethane A. A B. B C. C D. D Bloom's Level: 3. Apply Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.11 Subtopic: Bond formation and bond breaking Subtopic: Drawing and interpretation Topic: Curved Arrows 34. Which species is formed when the CH3N2 + cation loses a nitrogen molecule? A. A B. B C. C D. D Bloom's Level: 3. Apply Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.11 Subtopic: Bond formation and bond breaking Subtopic: Drawing and interpretation Topic: Curved Arrows 35. Give the molecular formula of the compound shown below: A. C8H16O B. C9H18O C. C10H18O D. C10H20O Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 36. The electron pair movement depicted below produces a second resonance form for the species. What is the formal charge on the nitrogen atom for this second resonance form? A. -2 B. -1 C. 0 D. +1 Bloom's Level: 3. Apply Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.07 Subtopic: Bond formation and bond breaking Subtopic: Drawing and interpretation Subtopic: Formal charges Subtopic: Resonance Topic: Curved Arrows Topic: Structure and Bonding 37. Which statement correctly describes the structures of BH3 and NH3? A. Both are trigonal and planar. B. Both are pyramidal. C. BH3 is trigonal planar and NH3 is trigonal pyramidal. D. BH3 is trigonal pyramidal and NH3 is trigonal planar. Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.09 Subtopic: VSEPR theory Topic: Molecular Shape 38. Which one of the following is the conjugate acid of ethanol? A. CH3CH2O - B. CH3CH2O + C. CH3CH2OH2+ D. CH3CH2OH3+ Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.12 Subtopic: Acid/Base definitions Topic: Acids and Bases 39. In the equilibrium below, the strongest base is: (pKa H2O = 15.7, pKa NH3 = 36) A. A B. B C. C D. D Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.14 Subtopic: Predicting acid/base reaction equilibrium Topic: Acids and Bases 40. In the equilibrium below, the strongest acid is: A. A B. B C. C D. D Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.14 Subtopic: Factors affecting acid strength Subtopic: Predicting acid/base reaction equilibrium Topic: Acids and Bases 41. Which one of the following is the strongest base? A. A B. B C. C D. D Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.13 Subtopic: Factors affecting acid strength Topic: Acids and Bases 42. Which one of the following mechanistically depicts the protonation of methanol by hydrogen bromide? A. A B. B C. C D. D Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.11 Subtopic: Curved arrow notation Topic: Curved Arrows 43. Which one of the following is the strongest acid? A. FCH2CO2H B. ClCH2CO2H C. BrCH2CO2H D. ICH2CO2H Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.13 Subtopic: Factors affecting acid strength Topic: Acids and Bases 44. Which one of the following has the largest acid equilibrium constant, Ka? A. CH3CO2H B. CH2ClCO2H C. CHCl2CO2H D. CCl3CO2H Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.13 Subtopic: Factors affecting acid strength Subtopic: pKa Topic: Acids and Bases 45. For which of the following does the equilibrium favor reactants? A. A B. B C. C D. D Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.14 Subtopic: Predicting acid/base reaction equilibrium Topic: Acids and Bases 46. Identify the resonance structure that results from the following "electron pair movements." A. A B. B C. C D. D Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.07 Subtopic: Resonance Topic: Structure and Bonding 47. A Lewis structure of the azide ion, N3¯, is shown below. The formal charge on the middle nitrogen atom is: A. +2 B. +1 C. 0 D. -1 Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.05 Subtopic: Formal charges Topic: Structure and Bonding 48. Identify the species that results from the following movement of electron pairs. A. A B. B C. C D. D Bloom's Level: 3. Apply Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.11 Subtopic: Bond formation and bond breaking Subtopic: Curved arrow notation Subtopic: Drawing and interpretation Topic: Curved Arrows 49. The most stable resonance contributor of this would be: A. A B. B C. C D. D Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.07 Subtopic: Resonance Topic: Structure and Bonding 50. What is the molecular formula of aspirin? A. C6H4O4 B. C8H8O4 C. C9H8O4 D. C9H10O4 Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 51. Which of the following is not identical to the others? A. A B. B C. C D. D Bloom's Level: 2. Understand Chapter: 01 Difficulty: Easy Gradable: automatic Section: 01.06 Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 52. Which of the line-bond structures below cannot represent a stable molecule? A. A B. B C. C D. D Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 53. Which of the electron-movement arrows below are NOT valid? A. A B. B C. C D. D Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.07 Subtopic: Resonance Topic: Structure and Bonding 54. What atom would have a formal charge in this structure? A. A B. B C. C D. D Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.05 Subtopic: Formal charges Topic: Structure and Bonding 55. Rank the following in order of decreasing acidity. (more acidic > less acidic) A. I > IV > III > II B. IV > I > II > III C. III > II > I > IV D. I > III > IV > II Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.13 Subtopic: Acid/Base definitions Subtopic: Factors affecting acid strength Topic: Acids and Bases 56. Using resonance principles, what atom is acid first protonated in the molecule shown? A. A B. B C. C D. D Bloom's Level: 4. Analyze Chapter: 01 Difficulty: Hard Gradable: automatic Section: 01.13 Subtopic: Acid/Base definitions Subtopic: Factors affecting acid strength Subtopic: Resonance Topic: Acids and Bases Topic: Structure and Bonding 57. What structure would result from these electron movement arrows? A. A B. B C. C D. D Bloom's Level: 3. Apply Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.07 Subtopic: Bond formation and bond breaking Subtopic: Curved arrow notation Subtopic: Drawing and interpretation Topic: Curved Arrows 58. What would be the line-bond structure for (CH3)3CCH2CH(CH3)2? A. A B. B C. C D. D Bloom's Level: 2. Understand Chapter: 01 Difficulty: Medium Gradable: automatic Section: 01.06 Subtopic: Condensed formula Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules Category # of Questions Accessibility: Keyboard Navigation 23 Bloom's Level: 1. Remember 1 Bloom's Level: 2. Understand 23 Bloom's Level: 3. Apply 23 Bloom's Level: 4. Analyze 11 Chapter: 01 58 Difficulty: Easy 5 Difficulty: Hard 16 Difficulty: Medium 37 Gradable: automatic 58 Section: 01.01 2 Section: 01.02 1 Section: 01.04 4 Section: 01.05 8 Section: 01.06 13 Section: 01.07 6 Section: 01.08 1 Section: 01.09 6 Section: 01.10 3 Section: 01.11 4 Section: 01.12 2 Section: 01.13 5 Section: 01.14 3 Subtopic: Acid/Base definitions 4 Subtopic: Atomic orbitals 1 Subtopic: Bond formation and bond breaking 5 Subtopic: Bond properties 4 Subtopic: Condensed formula 2 Subtopic: Constitutional isomers 3 Subtopic: Curved arrow notation 3 Subtopic: Dipole moments 3 Subtopic: Drawing and interpretation 5 Subtopic: Factors affecting acid strength 6 Subtopic: Formal charges 9 Subtopic: Hybridization 2 Subtopic: Octet rule exceptions 1 Subtopic: Periodic table trends 2 Subtopic: pKa 1 Subtopic: Polarity of molecules 3 Subtopic: Predicting acid/base reaction equilibrium 3 Subtopic: Resonance 6 Subtopic: Skeletal/bond-line structures 10 Subtopic: Types of bonds 4 Subtopic: VSEPR theory 5 Topic: Acids and Bases 10 Topic: Curved Arrows 6 Topic: Drawing Organic Molecules 13 Topic: Molecular Shape 10 Topic: Structure and Bonding 21 1. Alkanes are characterized by the general molecular formula: A. C nH2n-2 B. C nH2n C. C nH2n+2 C. C nH2n+4 Accessibility: Keyboard Navigation Bloom's Level: 1. Remember Chapter: 02 Difficulty: Easy Gradable: automatic Section: 02.05 Subtopic: Acyclic vs cyclic Subtopic: Alkanes Subtopic: Hydrocarbons Topic: Alkanes (Acyclic and Cyclic) Topic: Functional Groups 2. Cycloalkanes are characterized by the general molecular formula: A. C nH2n-2 B. C nH2n C. C nH2n+2 D. C nH2n+4 Accessibility: Keyboard Navigation Bloom's Level: 1. Remember Chapter: 02 Difficulty: Easy Gradable: automatic Section: 02.18 Subtopic: Acyclic vs cyclic Subtopic: Alkanes Subtopic: Hydrocarbons Topic: Alkanes (Acyclic and Cyclic) Topic: Functional Groups 2-1 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 3. The carbon-carbon sigma bond in ethane is formed by overlap of which two orbitals? A. 2p-2p B. sp-sp C. sp 2 -sp 2 D. sp 3 -sp 3 Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.07 Subtopic: Hybridization Topic: Molecular Shape 2-2 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 4.What is the IUPAC name of the following compound? A. 4,4-dimethylpentane B.1-tert-butylpropane C.2,2-dimethylpentane D. 1,1,1-trimethylbutane Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.17 Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 2-3 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 5.The correct IUPAC name of the following compound is A. 2-ethyl-3,5-dimethylheptane. B.6-ethyl-5,5-dimethylheptane. C.3,4,4-trimethyloctane. D. 5,5,6-trimethyloctane. Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.17 Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 6.The common name of the following group is A. n-butyl B. sec-butyl C. isobutyl D. tert-butyl Bloom's Level: 1. Remember Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.16 Subtopic: Alkyl groups Topic: Alkanes (Acyclic and Cyclic) 2-4 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 7. Which one of the following is 2,2,5-trimethylhexane? A. (CH3)2CHCH2C(CH3)3 B. (CH3)2CHCH2CH2C(CH3)3 C. CH3CH2CH(CH3)C(CH3)3 D. (CH3)2CHCH2CH2CH2C(CH3)3 Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.17 Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 8.The correct IUPAC name of the following is A. 2,4,7-trimethylnonane. B. 7-ethyl-2,4-dimethyloctane. C. 3,6,8-trimethylnonane. D. 2-ethyl-5,7-dimethyloctane. Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.17 Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 2-5 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 9.What is the IUPAC name of the following? A. 5,6-diethylhexane B. 5-ethyl-6-methylheptane C. 2,3-diethylhexane D. 4-ethyl-3-methylheptane Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.17 Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 10.What is the IUPAC name of the following? A. 1-ethyl-4.4-dimethylcyclopentane B.1-ethyl-3,3-dimethylcyclopentane C.3-ethyl-1,1-dimethylcyclopentane D. 4-ethyl-1,1-dimethylcyclopentane Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.18 Subtopic: IUPAC Nomenclature of cycloalkanes Topic: Alkanes (Acyclic and Cyclic) 2-6 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 11. Cyclohexane is composed of A. methine groups. B.methylene groups. C.methyl groups. D. both methine and methylene groups. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.11 Subtopic: IUPAC Nomenclature of cycloalkanes Topic: Alkanes (Acyclic and Cyclic) 12. All the carbons in cyclopentane are A. primary carbons. B.secondary carbons. C.tertiary carbons. D. quaternary carbons. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.16 Subtopic: IUPAC Nomenclature of cycloalkanes Topic: Alkanes (Acyclic and Cyclic) 2-7 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 13.The correct name of the following compound is A. (1-methylpropyl)cyclohexane. B.(2-methylpropyl)cyclohexane. C.(2,2-dimethylethyl)cyclohexane. D. (2,2-dimethylpropyl)cyclohexane. Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.18 Subtopic: IUPAC Nomenclature of cycloalkanes Topic: Alkanes (Acyclic and Cyclic) 2-8 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 14.The correct IUPAC name of the following compound is A. (1-methylhexyl)cyclopentane. B.(1-pentylethyl)cyclopentane. C.2-cyclopentylheptane. D. 1-cyclopentyl-2-heptane. Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.18 Subtopic: IUPAC Nomenclature of cycloalkanes Topic: Alkanes (Acyclic and Cyclic) 15.The C-C sigma bond in acetylene is formed by the overlap of which two orbitals? A. 2p-2p B. sp-sp C. sp 2 -sp 2 D. sp 3 -sp 3 Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.09 Subtopic: Hybridization Topic: Molecular Shape 2-9 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 16.The boiling point of isobutane (-10.2° C) is lower than n-butane (-0.4° C) because isobutane has A. weaker intermolecular van der Waals forces. B. stronger intermolecular van der Waals forces. C. weaker dipole-dipole attractive forces. D. stronger dipole-dipole attractive forces. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.21 Subtopic: Intermolecular forces Topic: Functional Groups 17. Which of the following describes an atom or group of atoms that has similar chemical properties when it occurs in different compounds? A. hydrocarbon B.functional group C.paraffin D. isomer Accessibility: Keyboard Navigation Bloom's Level: 1. Remember Chapter: 02 Difficulty: Easy Gradable: automatic Section: 02.19 Subtopic: C-Z functional groups (Z = N, O, S, halogen) Subtopic: Hydrocarbons Topic: Functional Groups 2-10 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 18.Arrange the following isomeric alkanes in order of increasing boiling point. I. n-heptane II. 2,3-dimethylpentane III. 2,2,3-trimethylbutane A. I < II < III B. II < III < I C. III < I < II D. III < II < I Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.21 Subtopic: Intermolecular forces Topic: Functional Groups 19. The oxidation states of carbon range from A. 0 to +2. B. 0 to +4. C. -4 to 0. D. -4 to +4. Accessibility: Keyboard Navigation Bloom's Level: 1. Remember Chapter: 02 Difficulty: Easy Gradable: automatic Section: 02.23 Subtopic: Acyclic vs cyclic Topic: Alkanes (Acyclic and Cyclic) 2-11 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 20.Which of the following has(have) a higher oxidation state of carbon than the carbon in formaldehyde, H2C=O? I. CH3OH II. HCO2H III. H2CO3 A. I B. III C. II and III D. I, II, and III Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.23 Subtopic: Acyclic vs cyclic Topic: Alkanes (Acyclic and Cyclic) 21. The tert-butyl group can also be called A. 1,1-dimethylpropyl. B.1,1-dimethylethyl. C.2,2-dimethylpropyl. D. 2,2-dimethylethyl. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.16 Subtopic: Alkyl groups Topic: Alkanes (Acyclic and Cyclic) 2-12 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 22.Carbon atoms 1, 2, and 3 in the following structure are classified, respectively, as A. tertiary, primary, secondary. B. quaternary, secondary, secondary. C. quaternary, primary, tertiary. D. quaternary, secondary, tertiary. Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.16 Subtopic: Alkyl groups Topic: Alkanes (Acyclic and Cyclic) 23. Identify the isomer of C6H14 that only has primary and tertiary carbons. A. hexane B. 2,2-dimethylbutane C. 3-methylpentane D. 2,3-dimethylbutane Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 02 Difficulty: Hard Gradable: automatic Section: 02.16 Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 2-13 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 24.Why can heats of combustion of constitutional isomers of hydrocarbons be used to measure their stabilities? I. Combustion of constitutional isomers gives different final states. II. Combustion of constitutional isomers gives the same final states. III. Constitutional isomers of hydrocarbons have the same potential energies. IV. Constitutional isomers of hydrocarbons have different potential energies. A. only I B. only II C. I and III D. II and IV Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.22 Subtopic: Reactions of alkanes Topic: Alkanes (Acyclic and Cyclic) 25.The heats of combustion (-∆H° ) of heptane and 3,3-dimethypentane are 4,817 and 4,809 kJ/mol, respectively. Which statement is true? A. Heptane is 8 kJ/mol more stable then 3,3-dimethylpentane. B. 3,3-Dimethylpentane is 8 kJ/mol more stable than heptane. C. Stabilities cannot be compared since they are not isomers. D. Stabilities cannot be compared since they give different combustion products. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.22 Subtopic: Reactions of alkanes Topic: Alkanes (Acyclic and Cyclic) 2-14 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 26.The reaction of acetylene with hydrogen gas is shown below. Which statements are true concerning the reaction? I. Acetylene is oxidized to ethane. II. Acetylene is reduced to ethane. III. Carbon changes oxidation state from -1 to -3. IV. Hydrogen (from H2) changes oxidation state from 0 to +1. A. I and III B. II and IV C. I, III, and IV D. II, III, and IV Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.23 Subtopic: Reactions of alkanes Topic: Alkanes (Acyclic and Cyclic) 27. How many methine groups are there in isopropylcyclopentane? A. one B. two C. three D. four Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.11 Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 2-15 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 28. What is the total number of constitutional isomers with the formula C5H12? A. two B. three C. four D. five Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.13 Subtopic: Constitutional isomers Topic: Drawing Organic Molecules 29.What is the IUPAC name of the following? A. 6-isopropyl-3-methylnonane B. 2-ethyl-5-isopropyloctane C. 6-propyl-3-methylnonane D. 2-ethyl-5-propyloctane Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.17 Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 2-16 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 30. How many moles of O2 gas would be consumed in the complete combustion of 0.100 mole of C5H12? A. 0.100 mole O2 B. 0.400 mole O2 C. 0.800 mole O2 D. 1.60 mole O2 Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 02 Difficulty: Hard Gradable: automatic Section: 02.22 Subtopic: Reactions of alkanes Topic: Alkanes (Acyclic and Cyclic) 31.The systematic name of the following group is A. 5-ethyl-2-methylpentyl. B.1-ethyl-4-methylpentyl. C.6-methyl-3-heptyl. D. 2-methyl-5-heptyl. Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.16 Subtopic: Alkyl groups Topic: Alkanes (Acyclic and Cyclic) 2-17 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 32.What is the relationship between the two structures below? A. identical structures B. resonance forms C. constitutional isomers D. different compounds with different compositions Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.11 Subtopic: Constitutional isomers Topic: Drawing Organic Molecules 2-18 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 33.What is the IUPAC name of the following structure? A. 3-propylpentane B. 3-ethylhexane C. 2-ethylheptane D. 4-ethylpentane Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.17 Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 2-19 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 34.Which of the following are constitutional isomers? I. 2,3,3-dimethylhexane II. 2,2-diethylpentane III. 3-ethyl-2-methylheptane A. I and II B. I and III C. II and III D. they are all constitutional isomers Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.11 Subtopic: Constitutional isomers Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) Topic: Drawing Organic Molecules 35.What is the estimated C-C-C bond angle in the following model? A. 90o B. 109.5o C. 120o D. 180o Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.08 Subtopic: Hybridization Topic: Molecular Shape 2-20 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 36.What are the hybridizations of carbon atoms 2, 3, and 4 shown in the model below? A. sp, sp 2 , sp 2 B. sp, sp 2 , sp 3 C. sp, sp, sp 2 D. sp, sp, sp 3 Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.09 Subtopic: Hybridization Topic: Molecular Shape 2-21 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 37.Arrange the following hydrocarbons in order of increasing boiling point. I. pentane II. 2,2-dimethylpropane III. 2-methylbutane A. I < II < III B. I < III < II C. II < I < III D. II < III < I Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.21 Subtopic: Intermolecular forces Topic: Functional Groups 38. The 1,1-dimethylethyl group, -C(CH3)3, can also be called A. butyl. B. isobutyl. C. sec-butyl. D. tert-butyl. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.16 Subtopic: Alkyl groups Topic: Alkanes (Acyclic and Cyclic) 2-22 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 39.What is the relationship between the following two structures? A. identical structures B. resonance forms C. constitutional isomers D. different compounds with different compositions Bloom's Level: 2. Understand Chapter: 02 Difficulty: Easy Gradable: automatic Section: 02.11 Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 40. The sp3 orbitals of carbon in CH4 are formed from the A. three 2p orbitals. B. 2s and two of the 2p orbitals. C. 2s and one of the 2p orbitals. D. 2s and the three 2p orbitals. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.06 Subtopic: Hybridization Topic: Molecular Shape 2-23 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 41. The geometry of sp3 hybrid orbitals can be described as pointing towards the corners of a A. triangle. B. square. C. tetrahedron. D. square pyramid. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.06 Subtopic: Hybridization Topic: Molecular Shape 42. What is the Cl-C-Cl bond angle in CCl4? A. 60o B. 90o C. 109.5o D. 120o Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.08 Subtopic: Hybridization Topic: Molecular Shape 43. Which of the following has the lowest boiling point? A. pentane B. 2,2-dimethylpropane C. 2-methylbutane D. hexane Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.21 Subtopic: Intermolecular forces Topic: Functional Groups 2-24 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 44.The shortest and longest carbon-carbon bonds, respectively, in this molecule are: A. II and III B. IV and III C. I and IV D. IV and I Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.08 Subtopic: Bond properties Subtopic: Types of bonds Topic: Structure and Bonding 45. How many isomers of C6H14 are possible? A. four B. five C. six D. seven Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.15 Subtopic: Constitutional isomers Topic: Drawing Organic Molecules 2-25 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 46.Which of the molecules below is NOT an isomer of formula C6H14? A. A B. B C. C D. D Bloom's Level: 3. Apply Chapter: 02 Difficulty: Easy Gradable: automatic Section: 02.18 Subtopic: Constitutional isomers Subtopic: Skeletal/bond-line structures Topic: Drawing Organic Molecules 47. Which of the following statements is not true concerning hydrocarbons? A. Hydrocarbons are compounds that carbon, hydrogen, and oxygen atoms. B. Alkanes, alkenes, and alkynes are examples of aliphatic hydrocarbons. C. Aromatic hydrocarbons are also referred to as arenes. D. Hydrocarbons may contain sigma bonds and/or pi bonds. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Easy Gradable: automatic Section: 02.01 Subtopic: Alkanes Subtopic: Alkenes Subtopic: Alkynes Subtopic: Arenes (Aromatics) Subtopic: Hydrocarbons Topic: Functional Groups 2-26 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 48. How many isomers of C4H9Cl are possible? A. two B. three C. four D. five Accessibility: Keyboard Navigation Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.11 Subtopic: Constitutional isomers Topic: Drawing Organic Molecules 49. The smallest straight-chain alkane that is liquid at room temperature and atmospheric pressure is A. propane. B. butane. C. pentane. D. hexane. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.21 Subtopic: Intermolecular forces Topic: Functional Groups 2-27 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 50.The lowest-boiling isomer of C7H16 would be A. A. B. B. C. C. D. D. Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.21 Subtopic: Intermolecular forces Topic: Functional Groups 51.The C-C-C bond angle in propyne, shown below, is A. 90°. B. 109.5°. C. 120°. D. 180°. Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.09 Subtopic: Hybridization Topic: Molecular Shape 2-28 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 52.The hybridization of carbon atoms 1, 2, and 3 in the following are respectively, A. sp, sp, and sp2 . B.sp, sp, and sp3 . C.sp 2 , sp 2 , and sp3 . D. sp2 , sp 3 , and sp3 . Bloom's Level: 3. Apply Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.08 Subtopic: Hybridization Topic: Molecular Shape 53.How many pi bonds are present in the following structure? A. one B. two C. three D. four Bloom's Level: 2. Understand Chapter: 02 Difficulty: Easy Gradable: automatic Section: 02.09 Subtopic: Hybridization Topic: Molecular Shape 2-29 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 54.The carbon-carbon single bond in the following is formed by the overlap of which two orbitals? A. sp-sp B. sp 2 -sp C. sp 2 -sp 2 D. sp 2 -sp 3 Bloom's Level: 2. Understand Chapter: 02 Difficulty: Medium Gradable: automatic Section: 02.09 Subtopic: Hybridization Topic: Molecular Shape 2-30 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. Category # of Questions Accessibility: Keyboard Navigation 29 Bloom's Level: 1. Remember 5 Bloom's Level: 2. Understand 25 Bloom's Level: 3. Apply 20 Bloom's Level: 4. Analyze 4 Chapter: 02 54 Difficulty: Easy 8 Difficulty: Hard 2 Difficulty: Medium 44 Gradable: automatic 54 Section: 02.01 1 Section: 02.05 1 Section: 02.06 2 Section: 02.07 1 Section: 02.08 4 Section: 02.09 5 Section: 02.11 6 Section: 02.13 1 Section: 02.15 1 Section: 02.16 7 Section: 02.17 7 Section: 02.18 5 Section: 02.19 1 Section: 02.21 6 Section: 02.22 3 Section: 02.23 3 Subtopic: Acyclic vs cyclic 4 Subtopic: Alkanes 3 Subtopic: Alkenes 1 Subtopic: Alkyl groups 5 Subtopic: Alkynes 1 Subtopic: Arenes (Aromatics) 1 Subtopic: Bond properties 1 2-31 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. Subtopic: C-Z functional groups (Z = N, O, S, halogen) 1 Subtopic: Constitutional isomers 6 Subtopic: Hybridization 11 2-32 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. Subtopic: Hydrocarbons 4 Subtopic: Intermolecular forces 6 Subtopic: IUPAC Nomenclature of acyclic alkanes 10 Subtopic: IUPAC Nomenclature of cycloalkanes 5 Subtopic: Reactions of alkanes 4 Subtopic: Skeletal/bond-line structures 2 Subtopic: Types of bonds 1 Topic: Alkanes (Acyclic and Cyclic) 28 Topic: Drawing Organic Molecules 7 Topic: Functional Groups 10 Topic: Molecular Shape 11 Topic: Structure and Bonding 1 2-33 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 1.Identify the conformation of butane shown below. A. anti B. gauche C. skewed D. eclipsed Bloom's Level: 2. Understand Chapter: 03 Difficulty: Easy Gradable: automatic Section: 03.02 Subtopic: Conformations of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-1 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 2.What is the IUPAC name of the compound shown in the following Newman projection? A. 1,1,2,2-tetramethylethane B. 2,2,3,3-tetramethylbutane C. 1,2-dimethylethane D. 2,3-dimethylbutane Bloom's Level: 3. Apply Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.02 Subtopic: Conformations of acyclic alkanes Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-2 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 3.What is the IUPAC name of the compound shown below? A. 1,2,3-trimethylbutane B.2,3-dimethylpentane C.2,3,4-trimethylpentane D. 2-isopropylbutane Bloom's Level: 3. Apply Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.02 Subtopic: Conformations of acyclic alkanes Subtopic: IUPAC Nomenclature of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-3 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 4.What is the dihedral (torsion) angle between the two bromine atoms in the following sawhorse drawing? A. 0 o B. 30o C. 60o D. 90o Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.01 Subtopic: Conformations of acyclic alkanes Subtopic: Projections of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 5. At room temperature, the various conformations of butane A.do not interconvert; only the anti form is present. B. do not interconvert, but all conformations are present. C. interconvert very slowly. D. interconvert very rapidly. Accessibility: Keyboard Navigation Bloom's Level: 1. Remember Chapter: 03 Difficulty: Easy Gradable: automatic Section: 03.02 Subtopic: Conformations of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-4 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 6.Which statement is correct concerning the relative stabilities of the two conformations, A and B, below? A. A is more stable. B. B is more stable. C. A and B are equal in stabilities. D. A and B are not equal in stability, but the preferred conformation cannot be determined by inspection. Bloom's Level: 4. Analyze Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.12 Subtopic: Conformational analysis of cyclohexane Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 3-5 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 7.Identify the spatial relationship of the two chlorine atoms. A. gauche B. anti C. eclipsed D. twist Bloom's Level: 2. Understand Chapter: 03 Difficulty: Easy Gradable: automatic Section: 03.11 Subtopic: Conformational analysis of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 3-6 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 8.Which statement is correct concerning the relative stabilities of the two conformations, A and B, below? A. A is more stable. B. B is more stable. C. A and B are equal in stabilities. D. A and B are not equal in stability, but the preferred conformation cannot be determined by inspection. Bloom's Level: 4. Analyze Chapter: 03 Difficulty: Hard Gradable: automatic Section: 03.12 Subtopic: Conformational analysis of cyclohexane Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 3-7 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 9.What is the IUPAC name of the following compound? A. trans-1,4-dimethylcyclohexane B. trans-1,3-dimethylcyclohexane C. cis-1,4-dimethylcyclohexane D. cis-1,3-dimethylcyclohexane Bloom's Level: 3. Apply Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.11 Subtopic: Conformations of cyclohexane Subtopic: IUPAC Nomenclature of cycloalkanes Topic: Alkanes (Acyclic and Cyclic) 3-8 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 10.What is the dihedral (torsion) angle between the two bromine atoms in the wedge-anddash drawing below? A. 60o B. 90o C. 120o D. 180o Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.01 Subtopic: Conformational analysis of acyclic alkanes Subtopic: Projections of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-9 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 11.Identify the relationship between the following two structures. A. constitutional isomers B. stereoisomers C. different conformations of the same compound D. identical Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.09 Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 12. Predict which of the following constitutional isomers of C5H10 would have the highest heat of combustion? A. methylcyclobutane B.cyclopentane C.cis-1,2-dimethylcyclopropane D. trans-1,2-dimethylcyclopropane Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.11 Subtopic: Conformations of cyclic alkanes Subtopic: Reactions of alkanes Topic: Alkanes (Acyclic and Cyclic) 3-10 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 13.Identify the two atoms anti to the bromine. A. the equatorial H's on C-2 and C-6 B. C-2 and C-6 C. the axial H's on C-2 and C-6 D. C-3 and C-5 Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.08 Subtopic: Conformational analysis of cyclohexane Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 14.Cyclohexane adopts the chair conformation rather than a planar structure because I. torsional strain is minimized. II. the C-C-C bond angles are close to 109.5o . III. there are no 1,3-diaxial interactions in a planar structure. A. only I B. only II C. I and II D. I, II, and III Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.07 Subtopic: Conformational analysis of cyclohexane Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 3-11 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 15.Identify the relationship between the following two structures. A. constitutional isomers B. stereoisomers C. different conformations of the same compound D. identical Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.09 Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 3-12 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 16.The most stable conformation of the compound shown has A. all methyl groups equatorial. B. equatorial methyl groups at C-1 and C-2, axial at C-4. C. equatorial methyl groups at C-1 and C-4, axial at C-2. D. equatorial methyl groups at C-2 and C-4, axial at C-1. Bloom's Level: 4. Analyze Chapter: 03 Difficulty: Hard Gradable: automatic Section: 03.12 Subtopic: Conformational analysis of cyclohexane Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 17. The most stable chair conformation of cis-1-tert-butyl-3-methylcyclohexane has A. both groups equatorial. B. both groups axial. C. the tert-butyl group equatorial and the methyl group axial. D. the tert-butyl group axial and the methyl group equatorial. Accessibility: Keyboard Navigation Bloom's Level: 4. Analyze Chapter: 03 Difficulty: Hard Gradable: automatic Section: 03.12 Subtopic: Conformational analysis of cyclohexane Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 3-13 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 18.Identify the relationship of the two compounds below. A. identical B. constitutional isomers C. stereoisomers D. different conformations of the same compound Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.11 Subtopic: Polycyclic systems Topic: Alkanes (Acyclic and Cyclic) 3-14 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 19.Identify the correct stereoisomer and the most stable conformation of the following compound. A. A B. B C. C 3-15 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. D. D Bloom's Level: 4. Analyze Chapter: 03 Difficulty: Hard Gradable: automatic Section: 03.12 Subtopic: Conformational analysis of cyclohexane Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 20.Identify the relationship of the two compounds below. A. identical B. constitutional isomers C. stereoisomers D. different conformations of the same compound Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.11 Subtopic: Conformations of cyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-16 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 21.What is the IUPAC name of the following compound? A. bicyclo[2.2.2]octane B. bicyclo[3.3.3]octane C. bicyclo[2.2.2]hexane D. bicyclo[3.3.3]hexane Bloom's Level: 3. Apply Chapter: 03 Difficulty: Hard Gradable: automatic Section: 03.14 Subtopic: IUPAC Nomenclature of cycloalkanes Subtopic: Polycyclic systems Topic: Alkanes (Acyclic and Cyclic) 22. Which statement below is true concerning the conversion of cis1,4-dimethylcyclohexane to trans-1,4-dimethylcyclohexane? A. The conversion takes place by chair conformation ring-flipping. B. You cannot do the conversion without breaking covalent bonds. C. The conversion takes place by rotating the C(1)-C(2) bond by 180° . D. The conversion takes place through the skew boat conformations. Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.09 Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 3-17 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 23.What is the IUPAC name of the following bicycloalkane? A. bicyclo[6.3.0]heptane B. bicyclo[4.2.1]hexane C. bicyclo[4.1.0]hexane D. bicyclo[4.1.0]heptane Bloom's Level: 3. Apply Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.14 Subtopic: IUPAC Nomenclature of cycloalkanes Subtopic: Polycyclic systems Topic: Alkanes (Acyclic and Cyclic) 3-18 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 24.Identify the relationship between the following two structures. A. identical B. different conformations of the same compound C. stereoisomers D. constitutional isomers Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.11 Subtopic: Conformations of cyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-19 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 25.Which isomer of 1-tert-butyl-3-ethyl-5-methylcyclohexane below is thermodynamically the most stable? A. A B. B C. C D. D Bloom's Level: 4. Analyze Chapter: 03 Difficulty: Hard Gradable: automatic Section: 03.12 Subtopic: Conformational analysis of cyclohexane Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 3-20 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 26. What would the C-C-C bond angles be in a planar cyclohexane? A. 60o B. 90o C. 109.5o D. 120o Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 03 Difficulty: Easy Gradable: automatic Section: 03.04 Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 27.Identify the relationship between the following two Newman projections. A. identical B. stereoisomers C. different conformations of the same compound D. constitutional isomers Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.02 Subtopic: Conformations of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-21 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 28.The IUPAC name of the following compound is A. cis-1,2-dimethylcyclohexane. B. 1,1-dimethylcyclohexane. C. trans-1,2-dimethylcyclohexane. D. cis-1,3-dimethylcyclohexane. Bloom's Level: 3. Apply Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.07 Subtopic: Conformations of cyclohexane Subtopic: IUPAC Nomenclature of cycloalkanes Topic: Alkanes (Acyclic and Cyclic) 3-22 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 29.The following structure is A. cis-1,3-dimethylcyclohexane. B.cis-1,4-dimethylcyclohexane. C.trans-1,3-dimethylcyclohexane. D. trans-1,4-dimethylcyclohexane. Bloom's Level: 3. Apply Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.07 Subtopic: Conformations of cyclohexane Subtopic: IUPAC Nomenclature of cycloalkanes Topic: Alkanes (Acyclic and Cyclic) 3-23 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 30.The sawhorse drawing of butane below is A. a gauche conformation. B. the anti conformation. C. the least stable eclipsed conformation. D. the most stable eclipsed conformation. Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.02 Subtopic: Conformational analysis of acyclic alkanes Subtopic: Projections of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-24 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 31.The sawhorse drawing of butane below is the A. least stable staggered conformation. B.most stable staggered conformation. C.least stable eclipsed conformation. D. most stable eclipsed conformation. Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.02 Subtopic: Conformational analysis of acyclic alkanes Subtopic: Projections of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 32. Which constitutional isomer of dimethylcyclohexane does not exhibit cistrans isomerism? A. 1,1-dimethylcyclohexane B. 1,3-dimethylcyclohexane C. 1,2-dimethylcyclohexane D. 1,4-dimethylcyclohexane Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.11 Subtopic: Conformations of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 3-25 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 33.What is the estimated dihedral angle between the two methyl groups on the structure shown below? A. 30o B. 60o C. 90o D. 120o Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.12 Subtopic: Conformational analysis of cyclohexane Topic: Alkanes (Acyclic and Cyclic) 34. Which one of the following is a stereoisomer of trans-1,3-dimethylcyclopentane? A. 1,1-dimethylcyclopentane B. ethylcyclopentane C. cis-1,2-dimethylcyclopentane D. cis-1,3-dimethylcyclopentane Accessibility: Keyboard Navigation Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.11 Subtopic: Conformations of cyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-26 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 35.Which of the following best describes the conformation of propane shown below? A. C(1) - C(2) staggered and C(2) - C(3) staggered B. C(1) - C(2) staggered and C(2) - C(3) eclipsed C. C(1) - C(2) eclipsed and C(2) - C(3) staggered D. C(1) - C(2) eclipsed and C(2) - C(3) eclipsed Bloom's Level: 2. Understand Chapter: 03 Difficulty: Medium Gradable: automatic Section: 03.01 Subtopic: Conformational analysis of acyclic alkanes Subtopic: Projections of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-27 Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of McGraw-Hill Education. 36.Which one of the following is the butane conformation shown below? A. gauche B. anti C. skew D. eclipsed Bloom's Level: 2. Understand Chapter: 03 Difficulty: Easy Gradable: automatic Section: 03.02 Subtopic: Conformational analysis of acyclic alkanes Subtopic: Projections of acyclic alkanes Topic: Alkanes (Acyclic and Cyclic) 3-28 Copyright © 2016 McGraw-Hill