CHEM Review for Final Exam (all chapters). Central

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1 CHEM Review for Final Exam (all chapters). Central Multiple Choice Identify the choice that best completes the statement or answers the question. 1. Which of the following is/are primary (1 ) alcohols? a. only 1 b. only 3 c. only 1 and 3 d. only 2, 3, and 4 2. What is the IUPAC name of the following compound? a. (E)-2-methyl-3-penten-2-ol b. (Z)-2-methyl-3-penten-2-ol c. (E)-4-methyl-2-penten-4-ol d. (Z)-2-methyl-4-penten-2-ol 3. Which of the following has the highest boiling point? a. pentane b. methyl propyl ether c. diethyl ether d. 1-butanol 4. What is the major organic product obtained from the following reaction? pg. 1 CHEM Review for Final Exam (all chapters). Central

2 5. What is the best choice of reagent to achieve the following transformation? a. HCl b. Cl 2, light c. SOCl 2, pyridine d. HOCl, H 2O 6. What is the correct assignment of the names of the following ethers? = oxirane; 2 = oxetane; 3 = oxane b. 1 = oxirane; 2 = oxitane; 3 = oxane c. 1 = oxane; 2 = dioxane; 3 = oxetane d. 1 = oxirane; 2 = oxolane; 3 = oxane 7. Which of the following are thiols? pg. 2 CHEM Review for Final Exam (all chapters). Central

3 a. only 1 b. only 1 and 4 c. only 2 and 3 d. 1, 2, 3 and 4 8. What is the major organic product obtained from the following reaction? 9. What type of reactive intermediate is formed in the reaction of tert-butyl methyl ether with HBr to give tert-butyl bromide? a. tert-butyl anion b. tert-butoxide c. tert-butyl radical d. tert-butyl cation 10. What type of reactive intermediate is formed in the reaction of methyl propene with methanol in the presence of an acid catalyst to give methyl tert-butyl ether (MTBE)? a. tert-butyl cation b. tert-butyl radical c. tert-butyl anion d. tert-butoxide 11. What is the major organic product obtained from the following reaction? pg. 3 CHEM Review for Final Exam (all chapters). Central

4 a. only 1 b. only 2 c. only 3 d. both 2 and What is the best choice of reagent(s) to perform the following transformation? a. CH 3MgBr; followed by H 3O + b. H 2O, NaOH c. LiAlH 4 followed by H 3O + d. KMnO4 13. What is the major organic product obtained from the following reaction? 14. What is the major organic product obtained from the following reaction? pg. 4 CHEM Review for Final Exam (all chapters). Central

5 15. What is the major organic product obtained from the following reaction? 16. What would be the best choice of reagent(s) to perform the following transformation? a. H 2O 2 b. NaIO 4 c. H 2O, NaOH d. H 2SO Which feature in the 1 H NMR spectrum provides information about the number of types of different protons in a compound? a. number of signals b. integral c. splitting d. chemical shift 18. What is the splitting of the signal in the 1 H NMR spectrum for the methyl protons of 1-bromo-2-methylpropane? a. singlet b. doublet c. triplet d. nonet 19. What is the appearance of the signal corresponding to the CH 2 protons in the 1 H NMR spectrum of ethyl methyl ether, CH 3CH 2OCH 3? a. a doublet b. a triplet pg. 5 CHEM Review for Final Exam (all chapters). Central

6 c. a quartet d. a septet 20. What is the relative area of the six peaks in a sexet in an 1 H NMR spectrum? :2:3:3:2:1 b. 1:3:6:6:3:1 c. 1:5:10:10:5:1 d. 1:6:15:15:6:1 21. Which of the protons in the following molecule appear at the highest δ-value in the 1 H NMR spectrum? a. i b. ii c. iii d. iv 22. How many signals appear in the proton-decoupled 13 C NMR spectrum of 1,4-dibromobenzene? 23. How many signals appear in the proton-decoupled 13 C NMR spectrum of 1,3-dibromobenzene? 24. How many signals appear in the proton-decoupled 13 C NMR spectrum of 1,2-dibromobenzene? 25. The chemical shift of the protons of acetone, CH 3COCH 3, is 2.1 ppm when the spectrum is obtained at 250 MHz. What is the chemical shift of these protons when the spectrum is acquired at 500 MHz?.05 ppm.1 ppm c. 4.2 ppm d. 8.4 ppm 26. What is the IUPAC name of the following compound? pg. 6 CHEM Review for Final Exam (all chapters). Central

7 a. (E)-4-methyl-4-hepten-3-one b. (Z)-4-methyl-4-hepten-3-one c. (E)-4-methyl-3-hepten-5-one d. (Z)-4-methyl-3-hepten-5-one 27. What is the major organic product obtained from the following reaction? a. 2-phenyl-2-butanol b. 3-phenyl-2-butanol -phenylbutanone d. propiophenone, PhCOCH 2CH Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound? a. only 1 and 2 b. only 3 and 4 c. only 2 and 3 d. only 1, 2 and What is the major organic product obtained from the following sequence of reactions? pg. 7 CHEM Review for Final Exam (all chapters). Central

8 30. What is the major organic product obtained from the following reaction? 31. What is the major organic product obtained from the following reaction? a. 2-methyl-2-heptene b. 3-ethyl-2-pentene c. (Z) 2-methyl-3-heptene d. (E) 2-methyl-3-heptene 32. What is the major organic product obtained from the following reaction? pg. 8 CHEM Review for Final Exam (all chapters). Central

9 33. What is the major organic product obtained from the following reaction? 34. What is the major organic product obtained from the following reaction? a. 2-pentanol b. pentane c. 1-pentene d. (E) 2-pentene 35. What is the major organic product obtained from the following sequence of reactions? pg. 9 CHEM Review for Final Exam (all chapters). Central

10 36. What is the major organic product obtained from the following sequence of reactions? 37. Which of the following statements is not true? a. The reaction of a ketone with methanol in the presence of acid to give a acetal proceeds via a resonance stabilized cation b. Protonation of a ketone increases its electrophilicity c. The conversion of a hemiacetal to an acetal under acidic conditions proceeds via an S N1 mechanism d. The conversion of a hemiacetal to an acetal is catalyzed by both acid and base 38. What is the reactivity of Br 2 in the acid-catalyzed bromination of acetophenone? a. acid pg. 10 CHEM Review for Final Exam (all chapters). Central

11 b. base c. nucleophile d. electrophile 39. What is the major organic product obtained from the following reaction? 40. What is the major organic product obtained from the following reaction? 41. What is the best choice of reagent(s) to perform the following transformation? pg. 11 CHEM Review for Final Exam (all chapters). Central

12 . LiAlH 4; 2. H 3O + b. H 2, Pt c. 1. NaBH 4; 2. H 2O d. NaH 42. What is the IUPAC name of the following compound? a. dimethylamino-3-phenylpropanoic acid b. N,N-dimethyl 2-phenylethyl amide c. N,N-dimethyl 3-phenylpropanamide d. dimethyl 2-phenylpropanoylamine 43. What is the IUPAC name of the following compound? a. (E)-N-methyl 3-methyl-3-pentenamide b. (Z)-N-methyl 3-methyl-3-pentenamide c. (E)-1-methylamino-3-methyl-3-pentenal d. (Z)-1-methylamino-3-methyl-3-pentenal 44. What is the major organic product obtained from the following reaction? 45. What is the major organic product obtained from the following reaction? pg. 12 CHEM Review for Final Exam (all chapters). Central

13 46. What is the major organic product obtained from the following reaction? 47. What is the major organic product obtained from the following reaction? 48. What is the major organic product obtained from the following reaction? pg. 13 CHEM Review for Final Exam (all chapters). Central

14 49. What is the major organic product obtained from the following reaction? 50. What is the best choice of reagent(s) to achieve the following transformation? a. H 2O b. NaOH, H 2O c. 1. LiAlH 4; 2. H 3O + d. H 2SO What is the major organic product of the following sequence of reactions? pg. 14 CHEM Review for Final Exam (all chapters). Central

15 52. Which combination(s) of alkyl bromide and ester can be used to prepare the following product by reaction of the Grignard reagent derived from the alkyl bromide with the ester? a. only 1 b. only 3 c. only 1 and 3 d. only 2 and Which of the following compounds can be prepared by a mixed aldol condensation by treatment of a mixture of two carbonyl compounds and NaOH? pg. 15 CHEM Review for Final Exam (all chapters). Central

16 54. What is the major organic product obtained from the following reaction? 55. What is the major organic product obtained from the following reaction? pg. 16 CHEM Review for Final Exam (all chapters). Central

17 56. What is the correct order of exothermicity for hydrogenation of the following hexadienes upon treatment with H 2/Pd (more exothermic > less exothermic)? > 2 > 3 b. 3 > 1 > 2 c. 2 > 1 > 3 d. 3 > 2 > Which of the following arrangements of p atomic orbitals gives the highest energy π-antibonding molecular orbital of 1,3-butadiene? 58. What is (are) the major organic product(s) formed in the following reaction? a. only 1 b. only 2 c. only 1 and 3 d. only 2 and What are the units of absorbance, A, in ultraviolet-visible spectroscopy? a. J mol 1 b. nm mol 1 c. J mol 1 M 1 d. none, A is a dimensionless quantity 60. What are the units of ε in ultraviolet-visible spectroscopy? a. M 1 cm 1 pg. 17 CHEM Review for Final Exam (all chapters). Central

18 b. M cm c. J mol 1 M 1 d. none, ε is a dimensionless quantity 61. Which of the following represents the energy levels of the molecular orbitals of benzene? 62. Which orbital contains the lone pair on the nitrogen atom of pyridine? a. s b. p c. sp d. sp Which orbitals contain the lone pairs on the nitrogen atoms labeled i and ii in the imidazole ring? a. i = sp 2; ; ii = sp 3 b. i = p ; ; ii = sp 3 c. i = p ; ; ii = sp 3 d. i = p ; ; ii = sp Which of the following compounds is aromatic? a. ethane b. cyclobutadiene c. benzene d. cyclooctatetraene 65. Which of the following represents the energy levels of the molecular orbitals of cyclobutadiene? pg. 18 CHEM Review for Final Exam (all chapters). Central

19 66. What is the major organic product obtained from the following reaction? 67. What is the major organic product obtained from the following reaction? pg. 19 CHEM Review for Final Exam (all chapters). Central

20 68. What is the major organic product obtained from the following reaction? 69. What is the role of AlCl 3 in Friedel Crafts acylations using acid chlorides? a. Lewis acid b. electrophile c. base d. nucleophile 70. Which of the following sets of substituents are all activating groups in electrophilic aromatic substitution reactions? a. CH 3, OCH 3, COCH 3 b. Cl, CN, NO 2 c. Cl, NH 2, CH 3 d. CH 3, NH 2, OCH Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions? a. Cl, CN, NO 2 b. Cl, NH 2, CH 3 c. CH 3, OCH 3, COCH 3 d. CH 3, NH 2, OCH Which of the following reactions or sequences will provide 1-propylbenzene as the major product? a. treatment of benzene with isopropyl alcohol and HF b. treatment of benzene with propanoyl chloride and AlCl 3; followed by reaction with Zn(Hg) and HCl c. treatment of benzene with 1-chloropropane and AlCl 3 d. treatment of benzene with 1-propene and HF pg. 20 CHEM Review for Final Exam (all chapters). Central

21 73. Which of the following sets of reagents does not result in alkylation of benzene? a. tert-butyl chloride + AlCl 3 b. tert-butyl alcohol + H 3PO 4 c. methylpropene + HF d. methylpropane + H 2SO Why does anisole undergo bromination with Br 2 in the absence of FeBr 3 whereas bromination of benzene requires the presence of FeBr 3? a. anisole is a better nucleophile than benzene b. the methoxy group of anisole is an inductive electron withdrawing substituent c. Br 2 is a good nucleophile d. the reaction is accelerated by light 75. What is the major organic product obtained from the following reaction? 76. What is the major organic product obtained from the following sequence of reactions? pg. 21 CHEM Review for Final Exam (all chapters). Central

22 77. Which of the following is the reactive intermediate formed in the electrophilic nitration of nitrobenzene with HNO 3 and H 2SO 4? 78. Which mechanism accounts for the reaction of benzyl chloride with sodium cyanide to form cyanomethylbenzene (phenylacetonitrile, PhCH 2CN)? a. Bimolecular nucleophilic substitution (S N2) b. Nucleophilic aromatic substitution by elimination-addition c. Nucleophilic aromatic substitution by addition-elimination d. Electrophilic aromatic substitution 79. What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl 3 to give 4-chloro-1-tert-butylbenzene? a. Meisenheimer complex b. benzyne c. cyclohexadienyl cation d. benzyl radical 80. What type of intermediate is formed in upon irradiation of a mixture of toluene and chlorine to give benzyl chloride? a. Meisenheimer complex b. benzyne c. cyclohexadienyl cation d. benzyl radical 81. What is the IUPAC name of the following compound? a. (R)-4-amino-2-methylhexane b. (S)-4-amino-2-methylhexane c. N-ethyl N-(3-methylpropyl) amine d. (R)-3-amino-5-methylhexane pg. 22 CHEM Review for Final Exam (all chapters). Central

23 82. What is the IUPAC name of the following compound? -aminobicyclo[2.2.2]octane -aminobicyclo[2.2.2]octane c. 4-aminobicyclo[2.2.2]octane d. 2-aminobicyclo[6.4.4]octane 83. Which of the following is the strongest base? a. phenol b. aniline c. methylamine -nitroaniline 84. Which of the following will remove aniline from a solution of aniline in diethyl ether? a. aqueous KBr b. aqueous HCl c. aqueous NaOH d. aqueous CH 3COONa 85. What is the major organic product obtained from the following reaction? 86. What is the major organic product obtained from the following reaction? pg. 23 CHEM Review for Final Exam (all chapters). Central

24 87. What is the major organic product obtained from the following reaction? 88. What is the major organic product obtained from the following reaction? pg. 24 CHEM Review for Final Exam (all chapters). Central

25 89. What is the major organic product obtained from the following sequence of reactions? 90. What is the major organic product obtained from the following sequence of reactions? 91. What is the major organic product obtained from the following sequence of reactions? pg. 25 CHEM Review for Final Exam (all chapters). Central

26 92. What is the major organic product obtained from the following sequence of reactions? 93. What is the major organic product obtained from the following sequence of reactions? pg. 26 CHEM Review for Final Exam (all chapters). Central

27 94. Which combination of carbonyl compound and amine can be used to prepare the following product by reductive amination? a. only 1 b. only 3 c. only 1 and 3 d. only 2 and What is the major organic product obtained from the following reaction? pg. 27 CHEM Review for Final Exam (all chapters). Central

28 96. What is the major organic product obtained from the following reaction? 97. What is the major organic product obtained from the following sequence of reactions? pg. 28 CHEM Review for Final Exam (all chapters). Central

29 98. What is the major organic product obtained from the following reaction? 99. What is the major organic product of the following sequence of reactions? Completion Complete each statement. 1. If the K a of isopropyl alcohol is , the pk a of isopropyl alcohol. pg. 29 CHEM Review for Final Exam (all chapters). Central

30 Consider the following reagents. 1. H 2CrO 4 2. PCC 3. PCl 3 4. SOCl 2 Choose the correct reagent to carry out the following conversions by placing the appropriate number in the blank provided to the left of the statement. If more than one number applies, enter the numbers separated by commas. 2. Oxidation of a primary alcohol to a carboxylic acid. To answer the following question, consider the reaction below: 3. Provide the complete IUPAC name for the starting material in this reaction. 4. Consider the following species. This substance is a conjugate base than the substance shown below. 5. Consider the following structures. Structure(s) could be used to produce an aldehyde by reaction with PCC. Enter the number of the appropriate structure. If more than one structure is correct, enter the appropriate numbers separated by commas. Consider the reaction below to answer the following questions. 6. The reaction shown here is an example of a synthesis 7. Consider the following reaction. pg. 30 CHEM Review for Final Exam (all chapters). Central

31 The name of the aromatic product is. 8. When cyclopentene is treated with peroxyacetic acid, the product that forms is. For each of the compounds below tell how many signals you would expect the molecule to have in its normal, broadband hydrogen-decoupled 13 C NMR spectra. Enter the numerical value in the blank provided to the left of the structure. 9. Predict the splitting of each of the numbered hydrogen atoms in the structure below in a 1 H NMR spectrum. Identify as singlet, doublet, triplet, quartet, quintet, sextet, septet,... Place the correct splitting in the blank to the left of the number Consider the following structure. the blank to the left. Answer the following questions by placing the appropriate number in 12. The number of nonequivalent hydrogen atoms in this compound. 13. The number of signals in the hydrogen-decoupled 13 C NMR of this compound. Consider the reaction below to answer the following question(s). Use letters where appropriate to answer the questions. pg. 31 CHEM Review for Final Exam (all chapters). Central

32 14. The nucleophile in this reaction is. 15. The first step in the reaction mechanism is the protonation of the group. Consider each of the spectrum and answer the following questions using the appropriate number. 16. The peak labeled would allow the distinction of an aldehyde from a ketone based on this spectrum. Answer each of the following questions with the appropriate number. 17. The number of α-hydrogens in the following compound is. 18. In the following compound, the most acidic hydrogen atom(s) are numbered as. 19. Of the compounds shown below, the one numbered is an imine. pg. 32 CHEM Review for Final Exam (all chapters). Central

33 20. Of the compounds shown below, the one numbered is an enamine. 21. When CO 2 is bubbled through an ether solution of benzylmagnesium bromide, and the resulting mixture is acidified, is produced. 22. Ethyl propanoate (CH 3CH 2COOCH 2CH 3) can be prepared by the reaction of ethanol with acid. 23. Pentanoic acid can be converted to its methyl ester in very high yield by reaction with. 24. Consider the following spectrum of a carboxylic acid derivative. This spectrum indicates the presence of a group. Consider the following general structures. Use the Roman numeral of the substance to answer the following questions. 25. The substance that is the least reactive toward nucleophilic acyl substitution is. 26. The substance that is classified as an anhydride is. 27. Consider the following 1 H NMR spectrum. pg. 33 CHEM Review for Final Exam (all chapters). Central

34 The line indicated with the number would indicate the presence of a C=O group. 28. Consider the following reaction The name of the reactant that should be placed in the box is. Consider the following compounds. Use the numbers shown to answer the following questions. the word none. If none of the structures is applicable enter 29. A lactone is represented by the structure numbered. 30. In an aldol reaction the following substance could be produced by the reaction of benzaldehyde and. Enter the name of the substance. 31. The class of compound formed in the reaction of the following two substance is a(n). pg. 34 CHEM Review for Final Exam (all chapters). Central

35 Consider the following types of reactions: 1. aldol condensation 2. Claisen condensation 3. Robinson annulation 4. Dieckmann condensation 5. Michael reaction Classify the following reactions by placing the appropriate number in the blank Consider the reaction below to answer the following question(s): pg. 35 CHEM Review for Final Exam (all chapters). Central

36 Enter the appropriate letter in the blank for each the following statements. 36. The kinetically controlled product in this reaction is. 37. The product that results from 1,4-addition is. 38. Consider the following spectrum for a conjugated diene. If a similar spectrum were taken for a conjugated tetraene, the λ max would be than 217 nm. Consider the reaction below to answer the following question(s). Fill in the blank in the question with the appropriate letter. 39. The dienophile in the reaction is. Answer the following questions concerning sulfathiazole below by filling ieach blank with the appropriate response. pg. 36 CHEM Review for Final Exam (all chapters). Central

37 40. Assuming that the sulfur atom is sp 2 -hybridized, there are π-electrons in the sulfathiazole ring. 41. According to Hückel criteria, sulfathiazole is predicted to be. Consider the cycloheptatrienyl anion. Complete the following questions by filling in the blank with the appropriate word. 42. This anion has π electrons. 43. Consider the following two compounds. B A An ether solution containing these two substances was mixed with an aqueous 1 M NaOH solution. Substance will be found in the basic layer. 44. Consider the following compound. When treated with acidic K 2Cr 2O 7 the product would be classified as a. Consider the following structure. 45. If named as an annulene, the name would be [ ] annulene. 46. This structure contains π electrons. Consider the following structure. pg. 37 CHEM Review for Final Exam (all chapters). Central

38 The 1 H NMR spectrum of [14]annulene at 60 C shows two peaks, one at 0 ppm and one at 7.6 ppm. 47. The NMR data would seem to indicate that this compound is. 48. The ratio of peak areas, respectively for the 7.6 ppm and 0 ppm, peaks would be. Consider the following compounds. Use the number of the compound to answer the following question. Place the number in the blank provided. 49. The compound that is the most reactive to nitration is. 50. The compound that is the least reactive to nitration is. 51. The name of the expected product from the following reaction is. Consider the reaction below to answer the following question(s). Fill in the blank with the appropriate letter or response. 52. The nucleophile in the reaction is. 53. The Lewis acid catalyst in the reaction is. pg. 38 CHEM Review for Final Exam (all chapters). Central

39 54. This reaction proceeds (faster or slower) than when benzene is used. Consider the following compounds. Answer the following questions by filling in the blank with the appropriate number from the diagram or an appropriate term. 55. The ammonia ion of substance will have the smallest pk a. 56. Substance is a primary alkyl amine. 57. The IUPAC name of the product of the following reaction is. From the list provided below, choose the best reagent(s) for each step in the following synthesis. There is only one answer for each reaction. Enter the appropriate letter in the blank provided. a. NaBH 4, ethanol d. 1. NaNO 2, H 3O + b. KCN, acetone 2. CuCN, KCN c. 1. LiAlH 4, THF e. 1. SnCl 2, H 3O + 2. H 2O 2. NaOH, H 2O f. HNO 3, H 2SO Step 1 Consider the following substances. Complete the following statements using the appropriate number. 59. Substance is pyrrole. 60. Substance is pyridine. pg. 39 CHEM Review for Final Exam (all chapters). Central

40 61. During oxidative addition, the coordination (number) of the metal by two. Use the reaction types given below in answering the following questions relating to reaction conditions. A. Heck reaction B. Stille coupling C. Suzuki coupling D. Sonogashira coupling E. Alkene metathesis Place the appropriate letter in the blank provided. 62. involves the use of alkynyl complexes. 63. involves the use of organoboron compounds. 64. involves an interchange of alkenyl groups. 65. The following polymer segment can be produced using an olefinic metathesis reaction. To produce the polymer, the reaction is repeated many times. The name of the reactant is. Problem 1. What is the IUPAC name of the following compound? 2. What is the IUPAC name of the following compound (shown as a Fischer projection)? 3. What is the IUPAC name of the following compound (shown as a Fischer projection)? pg. 40 CHEM Review for Final Exam (all chapters). Central

41 4. What is the major organic product obtained from the following reaction? 5. What is the major organic product obtained from the following reaction? 6. What is the major organic product obtained from the following reaction? 7. What is the major organic product obtained from the following reaction? 8. What is the major organic product obtained from the following reaction? 9. What is the major organic product obtained from the following reaction? 10. What is the major organic product obtained from the following reaction? pg. 41 CHEM Review for Final Exam (all chapters). Central

42 11. What is the major organic product obtained from the following reaction? 12. What is the IUPAC name of the following compound (shown as a Fischer projection)? 13. What is the IUPAC name of the following compound? 14. What is the IUPAC name of the following compound? 15. What is the IUPAC name of the following compound? 16. What is the IUPAC name of the following compound? 17. Provide the structures of the sodium alkoxide and the alkyl iodide that would be the best starting materials for the preparation of the following compound by a Williamson ether synthesis. 18. Provide the structures of the sodium alkoxide and the alkyl iodide that would be the best starting materials for the preparation of the following compound by a Williamson ether synthesis. pg. 42 CHEM Review for Final Exam (all chapters). Central

43 19. What is the major organic product obtained from the following reaction? 20. What is the major organic product obtained from the following reaction? 21. What is the major organic product obtained from the following reaction? 22. What is the major organic product obtained from the following reaction? 23. What is the major organic product obtained from the following reaction? 24. Identify the compound (C 3H 7Cl) that gives the following 1 H NMR spectrum. pg. 43 CHEM Review for Final Exam (all chapters). Central

44 25. Identify the compound (C 4H 8O) that gives the following 1 H NMR spectrum. 26. Identify the compound (C 4H 8O) that gives the following 1 H NMR spectrum. 27. Identify the compound (C 8H 10O 2) that gives the following 1 H NMR spectrum. pg. 44 CHEM Review for Final Exam (all chapters). Central

45 28. Identify the compound (C 8H 10) that gives the following 1 H NMR spectrum. 29. What is the IUPAC name of the following compound? 30. What is the IUPAC name of the following compound? 31. What is the major organic product obtained from the following reaction? pg. 45 CHEM Review for Final Exam (all chapters). Central

46 32. What is the major organic product obtained from the following reaction? 33. What is the major organic product obtained from the following reaction? 34. What is the major organic product obtained from the following reaction? 35. What is the major organic product obtained from the following reaction? 36. What is the major organic product obtained from the following reaction? 37. What is the major organic product obtained from the following sequence of reactions? pg. 46 CHEM Review for Final Exam (all chapters). Central

47 38. What is the IUPAC name of the following compound? 39. What is the major organic product obtained from the following reaction? 40. What is the major organic product obtained from the following reaction? 41. What is the major organic product obtained from the following reaction? 42. What is the IUPAC name of the following compound? 43. What is the IUPAC name of the following compound? 44. What two organic compounds are obtained from the following reaction? pg. 47 CHEM Review for Final Exam (all chapters). Central

48 45. What two organic compounds are obtained from the following reaction? 46. What two organic compounds are obtained from the following reaction? 47. What is the major organic product obtained from the following reaction? 48. What is the major organic product obtained from the following reaction? 49. What is the major organic product obtained from the following reaction? pg. 48 CHEM Review for Final Exam (all chapters). Central

49 50. What is the major organic product obtained from the following reaction? 51. What is the major organic product obtained from the following reaction? 52. What is the major organic product obtained from the following reaction? 53. What is the major organic product obtained from the following reaction? 54. What is the major organic product obtained from the following sequence of reactions? 55. What is the IUPAC name of the following compound? pg. 49 CHEM Review for Final Exam (all chapters). Central

50 56. What are the two major organic products obtained from the following reaction? 57. What is the major organic product obtained from the following reaction? 58. Draw two resonance structures of the reactive intermediate that accounts for the formation of 1,2- and 1,4-addition products upon reaction of 1,3-butadiene with one equivalent of HBr. 59. Which of 1,3-cyclohexadiene and 1,4-cyclohexadiene has the greatest heat of hydrogenation (i.e., the most exothermic reaction with H 2 in the presence of a catalyst). Provide a brief explanation for your choice? 60. What is the IUPAC name of the following compound? 61. What is the major organic product obtained from the following reaction? 62. What is the major organic product obtained from the following reaction? pg. 50 CHEM Review for Final Exam (all chapters). Central

51 63. What is the major organic product obtained from the following reaction? 64. What is the major organic product obtained from the following reaction? 65. What is the major organic product obtained from the following sequence of reactions (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)? 66. What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)? pg. 51 CHEM Review for Final Exam (all chapters). Central

52 67. Provide the structure (a single resonance contributor) of the key intermediate in the electrophilic aromatic chlorination of nitrobenzene. 68. Provide the structure (a single resonance contributor) of the key intermediate in the following reaction. 69. Provide a brief explanation, based on features of the molecules, for the following difference in pk a values? CH 3NH 2 > PhNH What is the major organic product obtained from the following reaction? 71. What is the major organic product obtained from the following sequence of reactions? 72. What is the major organic product obtained from the following sequence of reactions? pg. 52 CHEM Review for Final Exam (all chapters). Central

53 73. What is the major organic product obtained from the following sequence of reactions? 74. What is the major organic product obtained from the following sequence of reactions? 75. What is the major organic product obtained from the following sequence of reactions? 76. What is the major organic product obtained form the following sequence of reactions? 77. What is the major organic product obtained form the following sequence of reactions? 78. What is the major organic product obtained form the following sequence of reactions? 79. What is the major organic product obtained from the following reaction? 80. What is the major organic product obtained from the following reaction? pg. 53 CHEM Review for Final Exam (all chapters). Central

54 81. What is the major organic product obtained from the following reaction? 82. What is the major organic product obtained from the following reaction? 83. What is the major organic product obtained from the following reaction? 84. What is the major organic product obtained from the following reaction? 85. What is the major organic product obtained from the following sequence of reactions? pg. 54 CHEM Review for Final Exam (all chapters). Central

55 CHEM Review for Final Exam (all chapters). Central Answer Section MULTIPLE CHOICE 1. ANS: B 2. ANS: A 3. ANS: D 4. ANS: B 5. ANS: C 6. ANS: D 7. ANS: A 8. ANS: C 9. ANS: D 10. ANS: A 11. ANS: C 12. ANS: C 13. ANS: B 14. ANS: B 15. ANS: C 16. ANS: B 17. ANS: A 18. ANS: B 19. ANS: C 20. ANS: C 21. ANS: D 22. ANS: B 23. ANS: D 24. ANS: C 25. ANS: B 26. ANS: A 27. ANS: A 28. ANS: D 29. ANS: A 30. ANS: A 31. ANS: B 32. ANS: D 33. ANS: B 34. ANS: A 35. ANS: B 36. ANS: A 37. ANS: D 38. ANS: D 39. ANS: C 40. ANS: B 41. ANS: B pg. 55 CHEM Review for Final Exam (all chapters). Central

56 42. ANS: C 43. ANS: A 44. ANS: B 45. ANS: B 46. ANS: A 47. ANS: D 48. ANS: C 49. ANS: B 50. ANS: C 51. ANS: A 52. ANS: B 53. ANS: A 54. ANS: C 55. ANS: B 56. ANS: B 57. ANS: C 58. ANS: B 59. ANS: D 60. ANS: A 61. ANS: C 62. ANS: D 63. ANS: D 64. ANS: C 65. ANS: A 66. ANS: B 67. ANS: B 68. ANS: B 69. ANS: A 70. ANS: D 71. ANS: A 72. ANS: B 73. ANS: D 74. ANS: A 75. ANS: B 76. ANS: A 77. ANS: B 78. ANS: A 79. ANS: C 80. ANS: D 81. ANS: A 82. ANS: B 83. ANS: C 84. ANS: B 85. ANS: C 86. ANS: B 87. ANS: C 88. ANS: A pg. 56 CHEM Review for Final Exam (all chapters). Central

57 89. ANS: A 90. ANS: B 91. ANS: B 92. ANS: A 93. ANS: A 94. ANS: C 95. ANS: D 96. ANS: D 97. ANS: A 98. ANS: B 99. ANS: A COMPLETION 1. ANS: ANS: 1 3. ANS: (R)-2-heptanol (R)-heptan-2-ol 4. ANS: weaker 5. ANS: I,II II,I 6. ANS: Williamson ether 7. ANS: phenol 8. ANS: cyclopentene oxide 1,2-epoxycyclopentane 9. ANS: 3 three pg. 57 CHEM Review for Final Exam (all chapters). Central

58 10. ANS: quartet 11. ANS: triplet 12. ANS: 3 three 13. ANS: 3 three 14. ANS: A 15. ANS: carbonyl ketone 16. ANS: ANS: 4 four 18. ANS: 2 two 19. ANS: 2 two 20. ANS: 3 three 21. ANS: phenylacetic acid pg. 58 CHEM Review for Final Exam (all chapters). Central

59 phenylethanoic acid 22. ANS: propanoic propionic 23. ANS: diazomethane 24. ANS: nitrile 25. ANS: II 26. ANS: ANS: ANS: methanol methyl alcohol 29. ANS: 1 one 30. ANS: cyclopentanone 31. ANS: enamine 32. ANS: ANS: ANS: ANS: 5 pg. 59 CHEM Review for Final Exam (all chapters). Central

60 36. ANS: D 37. ANS: C 38. ANS: greater longer 39. ANS: B 40. ANS: six ANS: aromatic 42. ANS: 8 eight 43. ANS: B 44. ANS: quinone 45. ANS: ANS: ANS: aromatic 48. ANS: 5:2 5 to 2 5/2 pg. 60 CHEM Review for Final Exam (all chapters). Central

61 49. ANS: 3 three 50. ANS: 4 four 51. ANS: 4-ethyl-1,3-dimethylbenzene 52. ANS: A 53. ANS: C 54. ANS: slower 55. ANS: 4 four 56. ANS: 2 two 57. ANS: 4-methylpentanamine 58. ANS: e 59. ANS: 2 two 60. ANS: 3 three 61. ANS: increases pg. 61 CHEM Review for Final Exam (all chapters). Central

62 62. ANS: D 63. ANS: C 64. ANS: E 65. ANS: 4-ethylcyclopentene PROBLEM 1. ANS: (R)-4-methylpent-4-en-2-ol 2. ANS: (S)-butan-2-ol 3. ANS: (R)-pentan-2-ol 4. ANS: 5. ANS: 6. ANS: 7. ANS: pg. 62 CHEM Review for Final Exam (all chapters). Central

63 8. ANS: 9. ANS: 10. ANS: 11. ANS: 12. ANS: (1S,3S)-3-methylcyclohexanol 13. ANS: 2-ethoxyethanol 14. ANS: 1,2-diethoxyethane pg. 63 CHEM Review for Final Exam (all chapters). Central

64 15. ANS: 1-methoxycyclohex-1-ene 16. ANS: dicyclopentyl ether (oxadicyclopentane) 17. ANS: 18. ANS: 19. ANS: 20. ANS: 21. ANS: pg. 64 CHEM Review for Final Exam (all chapters). Central

65 22. ANS: 23. ANS: 24. ANS: 1-chloropropane 25. ANS: butanal 26. ANS: 2-butanone 27. ANS: 3-phenylpropanoic acid, PhCH 2CH 2CO 2H 28. ANS: o-xylene (1,2-dimethylbenzene) 29. ANS: (S)-2-chloropentanal 30. ANS: (S)-3-methyl-2-pentanone 31. ANS: pg. 65 CHEM Review for Final Exam (all chapters). Central

66 32. ANS: 33. ANS: 34. ANS: 35. ANS: 36. ANS: 37. ANS: pg. 66 CHEM Review for Final Exam (all chapters). Central

67 38. ANS: (Z)-2-butenoic acid 39. ANS: 40. ANS: 41. ANS: 42. ANS: (Z)-ethyl 2-methyl-2-butenoate 43. ANS: (Z)-N,N-dimethyl-3-pentenamide 44. ANS: 45. ANS: pg. 67 CHEM Review for Final Exam (all chapters). Central

68 46. ANS: 47. ANS: 48. ANS: 49. ANS: 50. ANS: 51. ANS: pg. 68 CHEM Review for Final Exam (all chapters). Central

69 52. ANS: 53. ANS: 54. ANS: 55. ANS: (E)-2,3-dimethyl-1,3-pentadiene 56. ANS: 57. ANS: 58. ANS: pg. 69 CHEM Review for Final Exam (all chapters). Central

70 59. ANS: 1,4-Cyclohexadiene has a greater heat of hydrogenation. This is because 1,3-cyclohexadiene is stabilized by conjugation of the two pi bonds. 60. ANS: 3,4-dichloroaniline 61. ANS: 62. ANS: 63. ANS: 64. ANS: pg. 70 CHEM Review for Final Exam (all chapters). Central

71 65. ANS: 66. ANS: 67. ANS: 68. ANS: pg. 71 CHEM Review for Final Exam (all chapters). Central

72 69. ANS: The phenyl group of aniline can serve as a resonance electron withdrawing substitutent, thereby reducing the electron density of the nitrogen (relative to methyl amine) and lowering its basicity. 70. ANS: 71. ANS: 72. ANS: 73. ANS: 74. ANS: 75. ANS: pg. 72 CHEM Review for Final Exam (all chapters). Central

73 76. ANS: 77. ANS: 78. ANS: 79. ANS: 80. ANS: 81. ANS: 82. ANS: pg. 73 CHEM Review for Final Exam (all chapters). Central

74 83. ANS: 84. ANS: 85. ANS: pg. 74 CHEM Review for Final Exam (all chapters). Central