Test Bank For Organic Chemistry 9th Edition By John E. Mcmurry All Chapters 1-31 | Complete 2024/2025 | Verified.

Chapter 01 - Structure and Bonding 1. Give the ground-state electron configuration for carbon (atomic number 6). ANSWER: 1s 2 2s 2 2px 1 2py 1 or 1s 2 2s 2 2p 2 POINTS: 1 2. Give the ground-state electron configuration for fluorine (atomic number 9). ANSWER: 1s 2 2s 2 2px 2 2py 2 2pz 1 or 1s 2 2s 2 2p 5 POINTS: 1 3. Give the ground-state electron configuration for magnesium (atomic number 12). ANSWER: 1s 2 2s 2 2p 6 3s 2 POINTS: 1 4. How many electrons does silicon have in its valence shell? ANSWER: four POINTS: 1 Exhibit 1-1 Write valid Lewis (electron-dot) structures for each formula below. Show all electrons as dots and show all non-bonding electrons. 5. C2Cl4 tetrachloroethylene ANSWER: POINTS: 1 6. CO2 carbon dioxide ANSWER: POINTS: 1 7. CH4O methanol ANSWER: POINTS: 1 Exhibit 1-2 Consider the structure of urea, shown below, to answer the following question(s). 8. Refer to Exhibit 1-2. Fill in any non-bonding valence electrons that are missing from the line-bond structure. Cengage Learning Testing, Powered by Cognero Page 1 Chapter 01 - Structure and Bonding ANSWER: POINTS: 1 9. Refer to Exhibit 1-2. The carbon atom in urea is: a. sp 3 hybridized b. sp 2 hybridized c. sp hybridized d. not hybridized ANSWER: b POINTS: 1 10. Refer to Exhibit 1-2. The predicted NH2−C=O bond angle in urea is: a. 109.5° b. 120° c. 180° d. not predictable ANSWER: b POINTS: 1 Exhibit 1-3 Determine the hybridization for the indicated atoms in each structure below. 11. Refer to Exhibit 1-3. The hybridization of this oxygen atom (A) is ______. ANSWER: sp 2 POINTS: 1 12. Refer to Exhibit 1-3. The hybridization of this oxygen atom (B) is ______. ANSWER: sp 3 POINTS: 1 13. Refer to Exhibit 1-3. The hybridization of this carbon atom (C) is ______. ANSWER: sp 3 POINTS: 1 14. Refer to Exhibit 1-3. The hybridization of this carbon atom (D) is ______. ANSWER: sp POINTS: 1 Cengage Learning Testing, Powered by Cognero Page 2 Chapter 01 - Structure and Bonding 15. The molecular formula C2H4O can be converted into three-line bond (Kekulé) structures that are consistent with valence rules. a. b. c. d. a. Which one of the Kekulé structures is not consistent with valence rules? b. Explain why the structure you chose in part a is not consistent with valence rules. ANSWER: a. d b. The carbon bonded to the oxygen atom in structure d is pentavalent; it has 10 valence electrons. Carbon can only have eight valence electrons. In addition, the other carbon has only six valence electrons when it would prefer to have eight. POINTS: 1 16. The original question was combined with #15. This placeholder question is here to maintain the integrity of the numbering system between the printed copy and ExamView. Therefore, it has been marked "do not use on test" in ExamView's question information dialog. As a result, this placeholder question is automatically prevented from being chosen as a test question. ANSWER: Answer not provided. POINTS: 1 17. Convert the following structure to a skeletal drawing and give its molecular formula. ANSWER: Molecular formula: C5H7Br POINTS: 1 18. Draw an orbital picture for acetylene, C2H2. Clearly label each bond type and indicate the type of orbitals involved in each bond. Cengage Learning Testing, Powered by Cognero Page 3 Chapter 01 - Structure and Bonding ANSWER: POINTS: 1 Exhibit 1-4 Propose possible structures for a molecule that meets each of the following descriptions. 19. Refer to Exhibit 1-4. Contains two sp 3 hybridized carbons and two sp hybridized carbons. ANSWER: POINTS: 1 20. Refer to Exhibit 1-4. Contains one sp 3 hybridized carbon and two sp 2 hybridized carbons. ANSWER: POINTS: 1 21. Convert the following molecular model into a condensed structure and a skeletal structure. ANSWER: POINTS: 1 22. Convert the following molecular model into a condensed structure and a skeletal structure. Cengage Learning Testing, Powered by Cognero Page 4 Chapter 01 - Structure and Bonding ANSWER: POINTS: 1 23. Convert the following molecular model into a condensed structure and a skeletal structure. ANSWER: or more specifically; POINTS: 1 24. Indicate the hybridization on each of the carbon atoms indicated with a number in the molecular model shown. ANSWER: Carbon 1: sp 3 Carbon 2: sp 2 POINTS: 1 25. Draw the orbital diagram showing the ground-state electron configuration of sulfur. Cengage Learning Testing, Powered by Cognero Page 5 Chapter 01 - Structure and Bonding ANSWER: POINTS: 1 26. Fill in any nonbonding valence electrons that are missing from the following structural representation of the amino acid cysteine. ANSWER: POINTS: 1 27. There are two substances with the molecular formula C2H7N. Draw them and describe how they differ. ANSWER: The two structures differ in the number of hydrogen atoms and carbon atoms bonded to the nitrogen atom. The first structure contains the carbon atoms bonded in a two carbon chain while in the second structure the two carbons atoms are isolated from each other by the nitrogen atom. POINTS: 1 28. Overlap of the two atomic orbitals shown could result in a: a. σ bond b. π bond c. σ or π depending on the direction of the overlap. Cengage Learning Testing, Powered by Cognero Page 6 Chapter 01 - Structure and Bonding ANSWER: c POINTS: 1 29. Hybridization of the atomic orbitals shown would result in: a. sp 3 hybridization b. sp 2 hybridization c. sp hybridization ANSWER: b POINTS: 1 30. Which of the following represents a hybrid orbital? a. b. c. d. ANSWER: d POINTS: 1 31. What type of hybridization is exhibited by carbon in the following substance?: a. sp 3 hybridization Cengage Learning Testing, Powered by Cognero Page 7 Chapter 01 - Structure and Bonding b. sp 2 hybridization c. sp hybridization ANSWER: b POINTS: 1 32. What type of hybridization is exhibited by carbon in the following substance?: a. sp 3 hybridization b. sp 2 hybridization c. sp hybridization ANSWER: c POINTS: 1 33. What type of hybridization is exhibited by the nitrogen atom in the following substance and how many lone pairs are present on the nitrogen?: a. sp 3 hybridization and 1 lone pair b. sp 2 hybridization and l lone pair c. sp hybridization and 1 lone pair d. sp 3 hybridization and 2 lone pairs e. sp 2 hybridization and 2 lone pairs f. sp hybridization and 2 lone pairs ANSWER: a POINTS: 1 34. If all the missing bonds in the following structure are sigma bonds to hydrogen atoms, how many hydrogen atoms are missing from this structure? Atoms other than carbon are labeled. a. 7 Cengage Learning Testing, Powered by Cognero Page 8 Chapter 01 - Structure and Bonding b. 10 c. 12 d. 14 e. None of these is the correct number. ANSWER: e POINTS: 1 Cengage Learning Testing, Powered by Cognero Page 9 Chapter 02 - Polar Covalent Bonds; Acids and Bases Chapter_02_Polar_Covalent_Bonds_Acids_and_Bases Exhibit 2-1 Give the corresponding letter of the term that best matches the given definition. a. Brønsted-Lowry Acid f. Ionic Bond b. Brønsted-Lowry Base g. Covalent Bond c. Lewis Acid h. Polar-Covalent Bond d. Lewis Base i. Hydrophobic e. Electronegativity j. Hydrophilic 1. _____ Any species that accepts electrons. ANSWER: c POINTS: 1 2. _____ A bond between two atoms differing in electronegativity by 0.5 − 2. ANSWER: h POINTS: 1 3. _____ A term used to describe a "water loving" species. ANSWER: j POINTS: 1 4. _____ A compound that can donate a proton. ANSWER: a POINTS: 1 5. _____ The ability of an atom to attract the shared electrons in a covalent bond. ANSWER: e POINTS: 1 6. _____ A term used to describe a "water fearing" species. ANSWER: i POINTS: 1 7. _____ Any species that donates electrons. ANSWER: d POINTS: 1 8. _____ A bond between two atoms differing in electronegativity by 0.5. ANSWER: g POINTS: 1 9. _____ A compound that can accept a proton. ANSWER: b POINTS: 1 Cengage Learning Testing, Powered by Cognero Page 1 Chapter 02 - Polar Covalent Bonds; Acids and Bases 10. _____ A bond between two atoms differing in electronegativity by 2. ANSWER: f POINTS: 1 Exhibit 2-2 Calculate the formal charges on the indicated atoms in each compound below. 11. Refer to Exhibit 2-2. The formal charge on phosphorous (A) is ______. ANSWER: +1 POINTS: 1 12. Refer to Exhibit 2-2. The formal charge on oxygen (B) is ______. ANSWER: −1 POINTS: 1 13. Refer to Exhibit 2-2. The formal charge on carbon (C) is ______. ANSWER: −1 POINTS: 1 14. Refer to Exhibit 2-2. The formal charge on oxygen (D) is ______. ANSWER: +1 POINTS: 1 Exhibit 2-3 Phenylalanine is an amino acid that is essential to human nutrition. The representation below shows the structure of phenylalanine at physiological pH. Consider this structure to answer the following question(s). 15. Refer to Exhibit 2-3. Assign any formal charges to atoms in this representation of phenylalanine. ANSWER: POINTS: 1 Cengage Learning Testing, Powered by Cognero Page 2 Chapter 02 - Polar Covalent Bonds; Acids and Bases 16. Refer to Exhibit 2-3. The oxygen atom labeled A. has ______ non-bonding electrons. ANSWER: four POINTS: 1 17. Refer to Exhibit 2-3. The oxygen atom labeled B. has _____ bonding electrons. ANSWER: two POINTS: 1 Exhibit 2-4 Use the convention and the crossed arrow to show the direction of the expected polarity of the indicated bonds in the following compounds. 18. Refer to Exhibit 2-4. The C−F bond in fluorobenzene, ANSWER: POINTS: 1 19. Refer to Exhibit 2-4. The C−Si bond in tetramethylsilane, (CH3)4Si ANSWER: POINTS: 1 20. Refer to Exhibit 2-4. The C−O bond in furan, ANSWER: POINTS: 1 Exhibit 2-5 Label the acid, conjugate acid, base, and conjugate base in each reaction below. 21. ANSWER: POINTS: 1 Cengage Learning Testing, Powered by Cognero Page 3 Chapter 02 - Polar Covalent Bonds; Acids and Bases 22. ANSWER: POINTS: 1 Exhibit 2-6 Refer to the following equation to answer the question(s) below. Place the letter corresponding to the correct answer in the blank. 23. Refer to Exhibit 2-6. The strongest Brønsted-Lowry acid in the equation is ______. ANSWER: D POINTS: 1 24. Refer to Exhibit 2-6. The strongest Brønsted-Lowry base in the equation is ______. ANSWER: C POINTS: 1 25. Refer to Exhibit 2-6. Will this reaction take place as written? Explain. ANS WER: No, the reaction will not take place as written because the strongest acid reacts with the strongest base to give the weakest conjugate acid and the weakest conjugate base. D (pKa = 15.7) is a stronger acid than A (pKa = 18). POIN TS: 1 26. An acid with a low pKa: a. is a weak acid b. is a strong acid c. has a weak conjugate base d. both b and c ANSWER: d POINTS: 1 Cengage Learning Testing, Powered by Cognero Page 4 EMAIL ME: For help with report, Assignment, Essay and thesis writing Chapter 02 - Polar Covalent Bonds; Acids and Bases 27. Circle all the Lewis bases in the group of compounds below. ANSWER: POINTS: 1 28. Put a box around all the Lewis acids in the group of compounds below. ANSWER: POINTS: 1 29. Draw two resonance structures for the species below. ANSWER: POINTS: 1 Cengage Learning Testing, Powered by Cognero Page 5 Chapter 02 - Polar Covalent Bonds; Acids and Bases 30. Draw two resonance structures for the species below. ANSWER: POINTS: 1 31. Draw two resonance structures for the species below. ANSWER: POINTS: 1 Exhibit 2-7 Consider the acidity constants below to answer the following question(s). ACID STRUCTURE p Ka phenol 10.00 ethanol CH3CH2OH 16.00 water HOH 15.74 32. Refer to Exhibit 2-7. Which acid will be almost completely deprotonated by NaOH? ANSWER: phenol POINTS: 1 33. Refer to Exhibit 2-7. Which acid has the strongest conjugate base? ANSWER: Ethanol is the weakest acid (largest pKa) so its conjugate base, ethoxide, CH3CH2O−, will be the strongest base. POINTS: 1 Cengage Learning Testing, Powered by Cognero Page 6 Chapter 02 - Polar Covalent Bonds; Acids and Bases 34. Refer to Exhibit 2-7. Explain why phenol has a much lower pKa than ethanol. ANSWER : Phenol is more acidic (has a lower pKa) than ethanol because the phenoxide anion is resonance stabilized by the pi electrons in the ring. Ethoxide anion has no resonance stabilization. The negative charge is borne fully by oxygen. POINTS: 1 Exhibit 2-8 Consider the reaction below to answer the following question(s). 35. Refer to Exhibit 2-8. Using the curved arrow formalism, show the flow of electrons for this reaction. ANSWER: POINTS: 1 36. Refer to Exhibit 2-8. Label the acid and the base in the reaction. ANSWER: POINTS: 1 Cengage Learning Testing, Powered by Cognero Page 7 Chapter 02 - Polar Covalent Bonds; Acids and Bases Exhibit 2-9 Indole is pleasant smelling in highly dilute solutions and has been used in perfumery. Use the structure of indole, below, to answer the following question(s). 37. Refer to Exhibit 2-9. Indole can function as a Brønsted-Lowry acid in the presence of strong bases. Formulate a reaction, showing electron flow with arrows, that demonstrates this reactivity of indole. ANSWER: POINTS: 1 38. Refer to Exhibit 2-9. Indole can function as a Lewis base in the presence of strong acid. Formulate a reaction, showing electron flow with arrows, that demonstrates this reactivity of indole. ANSWER: POINTS: 1 39. The condensed structure for dimethyl ether looks symmetrical. However, dimethyl ether has a dipole moment. Draw a structure that explains this and indicate the expected direction of the molecular dipole moment. ANSWER: POINTS: 1 Exhibit 2-10 Consider the acid-base reaction below to answer the following question(s). Cengage Learning Testing, Powered by Cognero