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Test Bank for Organic Chemistry, 8th Edition

Test Bank for Organic Chemistry, 8th Edition delivers an efficient way to prepare, covering all important topics with clarity and precision.

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    1 Chapter 1—Structure and Bonding SHORT ANSWER 1. Give the ground-state electron configuration for carbon (atomic number 6). ANS: 1 s 2 2 s 2 2 p x 1 2 p y 1 or 1 s 2 2 s 2 2 p 2 2. Give the ground-state electron configuration for fluorine (atomic number 9). ANS: 1 s 2 2 s 2 2 p x 2 2 p y 2 2 p z 1 or 1 s 2 2 s 2 2 p 5 3. Give the ground-state electron configuration for magnesium (atomic number 12). ANS: 1 s 2 2 s 2 2 p 6 3 s 2 4. How many electrons does silicon have in its valence shell? ANS: four 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. C 2 Cl 4 tetrachloroethylene ANS: 6. CO 2 carbon dioxide ANS: 7. CH 4 O methanol

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    Structure and Bonding 2 ANS: 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. ANS: 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 ANS: b 10. Refer to Exhibit 1-2. The predicted NH 2 − C=O bond angle in urea is: a. 109.5 ° b. 120 ° c. 180 ° d. not predictable ANS: b

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    Chapter 1 3 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 ______. ANS: sp 2 12. Refer to Exhibit 1-3. The hybridization of this oxygen atom ( B ) is ______. ANS: sp 3 13. Refer to Exhibit 1-3. The hybridization of this carbon atom ( C ) is ______. ANS: sp 3 14. Refer to Exhibit 1-3. The hybridization of this carbon atom ( D ) is ______. ANS: sp 15. The molecular formula C 2 H 4 O 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. ANS: 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.

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    Structure and Bonding 4 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. ANS: Answer not provided. 17. Convert the following structure to a skeletal drawing and give its molecular formula. ANS: Molecular formula: C 5 H 7 Br 18. Draw an orbital picture for acetylene, C 2 H 2 . Clearly label each bond type and indicate the type of orbitals involved in each bond. ANS:

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    Chapter 1 5 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. ANS: 20. Refer to Exhibit 1-4. Contains one sp 3 hybridized carbon and two sp 2 hybridized carbons. ANS: 21. Convert the following molecular model into a condensed structure and a skeletal structure. ANS: 22. Convert the following molecular model into a condensed structure and a skeletal structure.

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    Structure and Bonding 6 ANS: 23. Convert the following molecular model into a condensed structure and a skeletal structure. ANS: or more specifically; 24. Indicate the hybridization on each of the carbon atoms indicated with a number in the molecular model shown. ANS: Carbon 1: sp 3 Carbon 2: sp 2

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    Chapter 1 7 25. Draw the orbital diagram showing the ground-state electron configuration of sulfur. ANS: 26. Fill in any nonbonding valence electrons that are missing from the following structural representation of the amino acid cysteine. ANS: 27. There are two substances with the molecular formula C 2 H 7 N. Draw them and describe how they differ. ANS: 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.

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    Structure and Bonding 8 MULTIPLE CHOICE 1. 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. ANS: C 2. Hybridization of the atomic orbitals shown would result in: a. sp 3 hybridization b. sp 2 hybridization c. sp hybridization ANS: B 3. Which of the following represents a hybrid orbital? a. c. b. d.

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    Chapter 1 9 ANS: D 4. What type of hybridization is exhibited by carbon in the following substance?: a. sp 3 hybridization b. sp 2 hybridization c. sp hybridization ANS: B 5. What type of hybridization is exhibited by carbon in the following substance?: a. sp 3 hybridization b. sp 2 hybridization c. sp hybridization ANS: C 6. 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

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    Structure and Bonding 10 e. sp 2 hybridization and 2 lone pairs f. sp hybridization and 2 lone pairs ANS: A 7. 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 b. 10 c. 12 d. 14 e. None of these is the correct number. ANS: E

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    1 Chapter 2—Polar Covalent Bonds; Acids and Bases SHORT ANSWER Exhibit 2-1 Give the 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 can accept electrons. ANS: c 2. _____ A bond between two atoms differing in electronegativity by 0.5 − 2. ANS: h 3. _____ A term used to describe a "water loving" species. ANS: j 4. _____ A compound that can donate a proton. ANS: a PTS: 1 5. _____ The ability of an atom to attract the shared electrons in a covalent bond. ANS: e 6. _____ A term used to describe a "water fearing" species. ANS: i

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    Polar Covalent Bonds: Acids and Bases 2 7. _____ Any species that can donate electrons. ANS: d 8. _____ A bond between two atoms differing in electronegativity by < 0.5. ANS: g 9. _____ A compound that can accept a proton. ANS: b 10. _____ A bond between two atoms differing in electronegativity by > 2. ANS: f 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 ______. ANS: +1 12. Refer to Exhibit 2-2. The formal charge on oxygen ( B ) is ______. ANS: − 1 13. Refer to Exhibit 2-2. The formal charge on carbon ( C ) is ______. ANS: − 1

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    Chapter 2 3 14. Refer to Exhibit 2-2. The formal charge on oxygen ( D ) is ______. ANS: +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). 5. Refer to Exhibit 2-3. Assign any formal charges to atoms in this representation of phenylalanine. ANS: 16. Refer to Exhibit 2-3. The oxygen atom labeled A . has ______ non-bonding electrons. ANS: four 17. Refer to Exhibit 2-3. The oxygen atom labeled B . has _____ bonding electrons. ANS: two

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    Polar Covalent Bonds: Acids and Bases 4 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, ANS: 19. Refer to Exhibit 2-4. The C − Si bond in tetramethylsilane, (CH 3 ) 4 Si ANS: 20. Refer to Exhibit 2-4. The C − O bond in furan, ANS: Exhibit 2-5 Label the acid, conjugate acid, base, and conjugate base in each reaction below. 21. ANS:

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    Chapter 2 5 22. ANS: 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 ______. ANS: D 24. Refer to Exhibit 2-6. The strongest Brønsted-Lowry base in the equation is ______. ANS: C 25. Refer to Exhibit 2-6. Will this reaction take place as written? Explain. ANS: 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 (p K a = 15.7) is a stronger acid than A (p K a = 18). 26. An acid with a low p K a : a. is a weak acid b. is a strong acid c. has a weak conjugate base d. both b and c ANS: d

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