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Test Bank for Organic Chemistry 7th edition by Loudon and Parise

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Test Bank for Organic Chemistry 7th edition by Loudon and Parise

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  1. Email: smtb98@gmail.com Telegram: https://t.me/solumanu Contact me in order to access the whole complete document. WhatsApp: https://wa.me/message/2H3BV2L5TTSUF1 Indicate the answer choice that best completes the statement or answers the question. smtb98@gmail.com Organic Chemistry2 smtb98@gmail.com 1. Classify the reaction:   a. electrocyclic b. cycloaddition c. sigmatropic reaction     2. Determine the relationship between the two compounds.   a. constitutional isomers b. a pair of enantiomers c. identical molecules d. a pair of diastereomers e. none of these choices         3. Dissolving hexane in water has   a. a large negative ∆S°.   b. a large positive ∆S°.   c. a large negative ∆G°.   d. a large negative ∆H°.   e. a large positive ∆H°. 4. Which of these is a meta-directing group that is also an activator?   a. –CHO   b. –I   c. –NMe3+   d. –NO2   e. there are no meta-directing activators 5. Choose the best reagent(s) for carrying out the conversion. Page 1

  2. Email: smtb98@gmail.com Telegram: https://t.me/solumanu Contact me in order to access the whole complete document. WhatsApp: https://wa.me/message/2H3BV2L5TTSUF1 Organic Chemistry2   a. PhMgBr, ether; then aqueous acid b. PhCH2MgBr, ether; then aqueous acid c. Ph3P=CHPh d. LiCuPh2, ether       6. Arrange the compounds in order of increasing acidity (least to most acidic.)   a. A < C < D < B b. A < D < C < B c. A < B < C < D d. C < A < B < D e. C < A < D < B         7. Which is true of the Claisen condensation?   a. The product is an a-ketoester.   b.  The enolate formed undergoes a nucleophilic acyl substitution reaction with a second molecule of ester.   c. The condensation can occur under both acidic and basic conditions.   d.  The starting materials are an ester enolate and an aldehyde or ketone. 8. Typical IR absorptions occur in the 650–3700 cm–1 wavenumber range. These result from energy absorption from IR radiation by  (Pay attention to your units!)   a. molecular vibrations that occur roughly 1013 to 1014 times per second.   b. molecular rotations that occur roughly 1013 to 1014 times per second.   c. molecular vibrations that occur roughly 10–13 to 10–14 times per second.   d. molecular vibrations that occur roughly 1010–1011 times per second   e. molecular vibrations that occur roughly 10–11 to 10–12 times per second. 9. What is the relationship between the two starred methyl groups in N-acetylvaline methyl ester? Page 2 complete document is available on https://solumanu.com/ *** contact me if site not loaded

  3. smtb98@gmail.com Organic Chemistry2 smtb98@gmail.com   a. constitutionally nonequivalent b. homotopic c. enantiotopic d. diastereotopic e. identical in every way         10. Select the equilibrium that lies farthest to the right.  a.   b.   c.   d.  11. Which compound would form the strongest complex with potassium ion? Email: smtb98@gmail.com Telegram: https://t.me/solumanu Contact me in order to access the whole complete document. WhatsApp: https://wa.me/message/2H3BV2L5TTSUF1 Page 3 complete document is available on https://solumanu.com/ *** contact me if site not loaded

  4. Organic Chemistry2   a. compound A b. compound B c. compound C d. compound D       12. Which letter corresponds to the set of protons that experience the greatest magnetic field when a sample of the compound is placed in the probe of an NMR spectrometer?   a. a b. b c. c     13. Consider the IUPAC systematic name of the alkane. The name of this compound is    a. 5-ethyl-2-methyl-3-propylheptane.   b. 3-ethyl-5-isopropylnonane.   c. 6-ethyl-4-isopropyloctane. Page 4 complete document is available on https://solumanu.com/ *** contact me if site not loaded

  5. d. 1,1-diethyl-3-isopropylhexane. e. None of the above is a correct name. smtb98@gmail.com Organic Chemistry2 smtb98@gmail.com     14. Which is the strongest acid?   a. compound A b. compound B c. compound C d. compound D       15. Which atomic orbital has two nodes?   a. 2p   b. 3p   c. 4s   d. 1s   e. none of these 16. Which is a correct Newman projection of 3-methylpentane?    a.    b.  Page 5 complete document is available on https://solumanu.com/ *** contact me if site not loaded

  6. Organic Chemistry2   c.  17. Which compound would be the most reactive towards ring bromination?    a. compound A b. compound B c. compound C d. compound D e. compound E         18. Which compound or ion has five p molecular orbitals?   a. compound A b. compound B c. compound C d. compound D       19. An arginine residue and a phenylalanine residue are located close to each other in a protein structure. Page 6

  7. smtb98@gmail.com Organic Chemistry2 smtb98@gmail.com Select the most favorable interaction(s) of arginine and phenylalanine.   a. offset stacking   b. edge-to-face interaction   c. pi-cation interaction 20. The —C≡N stretching frequency in the infrared spectrum occurs at about 2220 cm–1. The C—N stretching frequency should occur at about    a. 740 cm–1   b. 1010 cm–1   c. 1280 cm–1   d. 1820 cm–1 21. A multistep reaction A ⇌ B ⇌ C ⇌ D has the free energy-reaction coordinate diagram shown below. Which step of the reaction is rate-limiting in the forward direction?    a. the reaction of A to B b. the reaction of B to C c. the reaction of C to D     22. The structure of ATP is shown below. A nucleophile can react with which phosphorus atom? Page 7

  8. Organic Chemistry2   a. thea phosphorus only b. the b phosphorus only c. the g phosphorus only d. The a, b, and g phosphorus can all react with nucleophiles.       23. Select the correct name for PhCH2Br.   a. bromobenzene   b. bromobenzyl   c. phenyl bromide   d. benzyl bromide 24. Which of the reactions would have the largest Keq?   a. X = H b. X = OEt c. X = CN d. X = NO2 e. X = Br         25. When we say, “sodium ethoxide (Na+ EtO−) acts as a nucleophile,” we always mean   a. that the sodium ion accepts a pair of electrons from the electrophile.   b. that the oxygen donates a pair of electrons to a carbon atom.   c. that the oxygen donates a pair of electrons to a leaving group.   d. that the oxygen donates a pair of electrons to an electrophile other than hydrogen.   e. that the leaving group donates a pair of electrons to the electrophile. 26. Consider the compound:  Page 8

  9. smtb98@gmail.com Organic Chemistry2 smtb98@gmail.com   a. homotopic. b. enantiotopic. c. diastereotopic. d. constitutionally nonequivalent.       27. Which side is favored at equilibrium?    a. the left b. the right c. need to know pKa values of the individual acids before estimating d. the equilibrium depends on the temperature of the measurement, and thus can't be known e. neither, Keq = 1         28. Select the bridged bicyclic compound with the formula C8H12 that violates Bredt’s rule.   a. compound A b. compound B c. compound C d. compound D       29. Sodium chloride, an ionic compound, should be most soluble in which solvent? (e = dielectric constant) Page 9

  10. Organic Chemistry2   a. compound a b. compound b c. compound c d. compound d e. compound e         30. Select the equilibrium that most favors products at equilibrium.  a.   b.  c.   d.  e.  31. Which of the compounds would have the strongest C=C stretching absorption in its IR spectrum?   a. compound A b. compound B c. compound C d. compound D       32. Which ester cannot be used in a Claisen condensation? Page 10 complete document is available on https://solumanu.com/ *** contact me if site not loaded

  11. smtb98@gmail.com Organic Chemistry2 smtb98@gmail.com   a. compound A b. compound B c. compound C d. compound D       33. In IR spectroscopy, an absorption occurs any time    a. a vibration is located in a magnetic field.   b. vibrating bonds are conjugated.   c. any vibrating bond interacts with a light wave vibrating with the same frequency.   d. a vibrating dipole moment interacts with a light wave vibrating with the same frequency.   e. the mass of one atom involved in the vibration is much less than the mass of the others. 34. Four stereoisomers of the naturally occurring amino acid isoleucine are given. L-Isoleucine is the stereoisomer with the 2S,3S configuration. Identify this stereoisomer.   a. compound A b. compound B c. compound C d. compound D       35. Consider this molecule: Which bond is an sp2–sp3s bond?    a. bond (a)   b. bond (b) Page 11

  12. Organic Chemistry2   c. bond (c) d. bond (d) e. bond (e)     36. Which compound decarboxylates fastest?   a. compound A b. compound B c. compound C d. compound D e. compound E         37. Which compound undergoes the fastest SN2 reaction with Na+ CH3O−?   a. CH3CH2Cl   b. (CH3)2CHCH2Br   c. (CH3)3CBr   d. CH3CH2Br   e. CH3CH2F 38. In this pair of compounds, identify the more stable one (as measured by heats of formation).   a. Compound a b. Compound b   39. The C=C stretching absorption in the IR spectrum occurs at about 1650 cm–1. The C—C stretching vibration occurs but is not observed. Which of these frequencies would be closest to the frequency of the C—C stretching vibration?   a. 3300 cm–1   b. 815 cm–1 Page 12

  13. c. 2330 cm–1 d. 1165 cm–1 e. (1650 cm–1)/2pc, where c is the speed of light. smtb98@gmail.com Organic Chemistry2 smtb98@gmail.com       40. Bases can catalyze nucleophilic addition reactions of aldehydes and ketones by   a. shifting the equilibrium of the reaction.   b. converting water to hydroxide ion, a much better nucleophile.   c. making the carbonyl group more electrophilic.   d. making the carbonyl group less electrophilic. 41. Which substrate will undergo the reaction the fastest?     a. compound A b. compound B c. compound C d. compound D       42. In an NMR spectrometer operating at ν0 = 300 MHz, a resonance that has a chemical shift of 2.0 ppm (i.e., d 2) occurs at a frequency that is   a. 600 Hz greater than the absorption frequency of the standard TMS.   b. 600 × 106 Hz greater than the absorption frequency of TMS   c. 150 Hz greater than the absorption frequency of TMS.   d. 150,000,000 Hz greater than the absorption frequency of TMS.   e. 302 Hz greater than the absorption frequency of TMS.   f. less than the absorption frequency of TMS. 43. Consider the bolded protons in 1-propanol.  Following a “D2O shake,” the splitting of the 1-propanol protons shown in bold type should be observed as   a. a singlet.   b. a doublet.   c. a triplet. Page 13

  14. Organic Chemistry2   d. a quartet. e. some other splitting.   44. Behold the structure of vanillin, which is the main ingredient in vanilla extract.  The functional groups in vanillin are best described as   a. a ketone, a phenol, and an ether.   b. an alcohol, an aldehyde, and an ether.   c. a ketone, an alcohol, and an ether.   d. a phenol, an aldehyde, and an ether.   e. an aldehyde, a phenol, and an alcohol. 45. Which reagent is used in the Stille coupling?   a. compound A b. compound B c. compound C d. compound D       46. Classify the reaction:   a. electrocyclic Page 14

  15. 47. Select the structure of the compound with the highest boiling point. smtb98@gmail.com Organic Chemistry2 smtb98@gmail.com   b. cycloaddition c. sigmatropic reaction     a. compound a b. compound b c. compound c d. compound d       48. According to the rate law for the SN2 reaction, doubling the nucleophile concentration (without changing the concentration of the electrophilic compound) should (select one)   a. decrease the reaction rate.   b. increase the reaction rate by a factor of √2.   c. increase the reaction rate by a factor of 2.   d. increase the reaction rate by a factor of 22, or 4.   e. increase the reaction rate by some other factor. 49. According to molecular orbital theory, which one of these species does not exist?   a.    b.    c.    d.    e. CH4 50. Choose the best reagent(s) for carrying out the conversion.   a. Mg, ether; CO2; then aqueous acid b. NaCN; then aqueous acid c. Both sets of reagents would work equally well. d. Neither set of reagents would work well.       51. When DMSO dissolves potassium chloride (K+ Cl−), what is the solvation of the salt due to? Page 15 complete document is available on https://solumanu.com/ *** contact me if site not loaded

  16. Organic Chemistry2   a. The charge–dipole interaction of the sulfur with the K+. b. The charge–dipole interaction of the oxygen with the K+. c. The charge–dipole interaction of the oxygen with the Cl−. d. The hydrogen-bonding interaction of the chloride ion with the C—H bonds.       52. Select the true statement.   a.  The S—H stretching absorption in the IR should occur at higher wavenumber than the C—H stretching absorption primarily because S has a greater mass than C.   b.The S—H stretching absorption in the IR should occur at higher wavenumber than the C—H stretching absorption primarily because the S—H bond is weaker than the C—H bond.   c.  The S—H stretching absorption in the IR should occur at lower wavenumber than the C—H stretching absorption primarily because the S—H bond is stronger than the C—H bond.   d.The S—H stretching absorption in the IR should occur at lower wavenumber than the C—H stretching absorption primarily because the S—H bond is weaker than the C—H bond.   e.  The S—H stretching absorption in the IR should occur at lower wavenumber than the C—H stretching absorption primarily because S has a greater mass than C. 53. Which reagents could be used to synthesize PhCOOH?    a. PhCO2CH3 in acidic methanol   b. PhCOCl + LiAlH4 followed by treatment with acid   c. PhCO2CH3 in aqueous base followed by treatment with acid   d. More than one of these would work.   e. None of these would work. 54. Which species shown would not be detected in the electron ionization (EI) mass spectrometry?   a. species Page 16 complete document is available on https://solumanu.com/ *** contact me if site not loaded

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