Study Union: CHM 2210 Final Exam Review 1. The following molecules are related in what manner?

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1 Study Union: CHM 2210 Final Exam Review 1. The following molecules are related in what manner? A) They are isotopes B) They are constitutional isomers C) They are the same structure D) They are composed of different elements E) There is no relationship 2. Which of the following structures represent compounds that are constitutional isomers? A) I, II B) III, IV C) I, II, III D) II, III, IV E) All of the compounds are constitutional isomers 3. Considering atoms with no formal charge, which statement best describes the valence of carbon, nitrogen, and oxygen? A) Carbon: two bonds, zero lone pairs; nitrogen: three bonds, two lone pairs B) xygen: two bonds, two lone pairs; nitrogen: three bonds, one lone pair C) Carbon: three bonds, one lone pair; oxygen: two bonds, two lone pairs D) Carbon: four bonds, zero lone pairs; nitrogen: two bonds, two lone pairs E) xygen: three bonds, one lone pair; nitrogen: two bonds, two lone pairs

2 4. In which of the following does the central atom have 2 pairs of non bonding electrons? A) 3 B) C2 C) C3 2 D) NH4 + E) H2S 5. In ammonium, nitrogen has a valence of 4, and zero nonbonding electrons. What is the correct formal charge of nitrogen with 4 covalent bonds? A) 2 B) 1 C) 0 D) +1 E) In which structure(s) below does the oxygen have a formal charge of +1? A) I only B) II only C) I and III D) I and IV E) I, III, and IV 7. Identify the hybridized orbitals involved in formation of the C N sigma ( ) bond in the following molecule known as an oxime: A) (sp 2, sp 2 ) B) (sp 3, sp 3 ) C) (sp, sp) D) (sp 2, sp 3 ) E) There is no sigma bond between C N.

3 8. From left to right, indicate the hybridization of the indicated atoms in the following molecule: A) I sp ; II sp 2 ; III sp 3 ; IV sp 2 B) I sp 2 ; II sp ; III sp 2 ; IV sp 3 C) I sp 3 ; II sp 2 ; III sp ; IV sp 2 D) I sp 2 ; II sp 3 ; III sp 2 ; IV sp E) I sp 2 ; II sp 2 ; III sp 2 ; IV sp 3 9. The carbon and oxygen atoms in carbon monoxide (C) are connected by which type of bond(s)? A) A sigma ( ) bond B) Two sigma ( ) bonds C) A pi ( ) bond D) Two pi ( ) bonds E) Both A and D 10. What is the approximate bond angle around the carbon in formaldehyde, a molecule with the formula H2C? A) 60 B) 90 C) D) 120 E) In the following reaction, how many H s do you add or lose? A. Add 1 B. Add 2 C. Lose 1 D. No change 12. In the following reaction, how many H s do you add or lose?

4 A. Add 1 B. Add 2 C. Lose 1 D. No change 13. Which of the following structures contains an aromatic ring? A. 1 B. 2 C. 3 D Which of the following pairs of structures are resonance structures? A. 1 B. 2 C. 3 D Which of the following is a correct resonance structure of A? A. 1 B. 2 C. 3 D Which of the following is a correct resonance structure of A? A. 1 B. 2 C. 3 D. 4

5 17. Which of the following is a correct resonance structure of A? H A A. 1 B. 2 C. 3 D. 4 E Which of the following is a valid resonance pair? A) B) C) D) none of the above 19. The indicated lone pairs in the following compounds are: i) ii) A. i) localized ii) delocalized B. i) localized ii) localized C. i) delocalized ii) localized D. i) delocalized ii) delocalized 20. How many resonance structures does the following compound have (including itself)? A. 1 B. 2 C. 3 D. 4 E. 5

6 21. In the following reaction, identify the acid and base as well as the conjugate acid and base. i ii iii iv A. i) Acid, ii) Base, iii) Conjugate acid, iv) Conjugate base B. i) Base, ii) Acid, iii) Conjugate acid, iv) Conjugate base C. i) Base, ii) Acid, iii) Conjugate base, iv) Conjugate acid D. i) Acid, ii) Base, iii) Conjugate base, iv) Conjugate acid E. None of the above 22. What is wrong with the following arrow? A. It should start on the alkyne carbon. B. It should start on a hydrogen attached to the nitrogen. C. It should start on the anion on nitrogen, end at the H on the alkyne, and a second arrow should start at the bond between the C and H on the alkyne and end on the terminal carbon of the alkyne. D. There should be two arrows one from nitrogen and one from the alkyne carbon. 23. Which side will the following acid-base reaction favor? A. The right B. The left C. Neither

7 24. For the following acid-base reaction, which procedure represents the best usage of arrow pushing and correct product formation? H

8 A. H + H 2 H B. H + H 2 H C. H + H 2 H D. H + H 2 H E. None of the above 25. Which side will the following acid-base reaction favor?

9 A. The right B. The left C. Neither 26. Identify the Lewis base in the following reaction. 27. Identify the Lewis base in the following reaction. 28. Which is the best descriptor for the following compound? A. onsted-lowry Acid B. onsted-lowry Base C. Lewis Acid D. Lewis Base E. Both B and D 29. Could water protonate the following compound? A. Yes B. No 30. What is the IUPAC name for the following compound? A. 2,3,5-triethylhexane B. 2,4,5-triethylhexane C. 2,4-diethyl-5-methylheptane D. 4-ethyl-3,6-dimethyloctane

10 31. What is the IUPAC name for the following compound? A. 1-ethyl-2-methylcyclohexane B. 2-ethyl-1-methylcyclohexane C. 1-ethyl-2-methylhexane D. cyclononane 32. What is the common name of the following substituent? A. isopropyl B. tert-butyl C. iso-butyl D. sec-butyl 33. What is the IUPAC name for the following compound? A. 3-isopropyl-5-ethylheptane B. 2-methyl-3-ethyl-5-ethylheptane C. 3,5-diethyl-2-methylheptane D. 2-methyl-3,5-diethylheptane 34. How many constitutional isomers does C6H14 have? A. 3 B.4 C.5 D.6 E Which of the following compounds are constitutional isomers?

11 A. 1 and 2 B. 2 and 3 C. 3 and 4 D. 1 and 3 E. none of these 36. Using Newman projection to determine the conformation between Cl and substituents in the following compound. A. Gauche B. Anti C. Eclipsed D. Syn E. none of these 37. Which of the following is a Newman projection for the following compound as viewed down the indicated bond? 38. Which of the following is the most stable conformer of the most stable isomer of 1,4-diethylcyclohexane? 39. Rank the following conformers of the isomers of 1-ethyl-2,4- dimethylcyclohexane from most to least stable. A. B. C. D. i ii iii A. iii>iv>ii>i B. ii>i>iii>iv C. iv>i>iii>ii

12 D. i>iii>ii>iv E. none of the above 40. How many chiral centers does these two compounds have in total? A) 5 B) 6 C) 7 D) 8 E) Are the following alkenes cis, trans, or neither? Me A) i) trans; ii) trans B) i) trans; ii) neither C) i) cis; ii) trans D) i) neither; ii) trans E) none of the above i) ii) F F 42. Identify the relationship between the following two structures. A. Enantiomers B. Identical C. Diastereomers D. Constitutional isomers E. None of the above 43. which of the following is the correct structure for a compound with the IUPAC name (R)-2-pentanol?

13 44. Which of the following is the correct IUPAC name for the following structure? A. (S)-3-ethyl-2-methylhexane B. (R)-3-ethyl-2-methylhexane C. (S)-3-ethyl-2-methylpentane D. (R)-3-ethyl-2-methylpentane 45. Rank the following from highest to lowest priority. i) -CH3 ii) -CN iii) -CH2H iv) - A) iii>i>ii>iv B) ii>iii>iv>i C) iii>ii>i>iv D) iv>iii>ii>i E) iv>ii>iii>i 46. Identify the relationship between the following two structures. H H H H HH 2 C CH HC CH 2 H H H H H H H H H A. Enantiomers B. Identical C. Diastereomers D. Constitutional isomers E. None of the above

14 47. (2R,3S)-Dibromobutane is: A. optically active. B. racemic. C. dextrorotatory. D. a meso compound. 48. Assign R or S configuration to each chirality center indicated in streptimidone. (i) (ii) a. (i) S; (ii) S b. (i) S; (ii) R c. (i) R; (ii) R d. (i) R; (ii) S 49. Which of the following structures is the correct wedge/dash drawing of the following Fischer projection? 50. Assign the following stereocenter as R or S. A. R B. S C. there is no chiral center on this compound. 51. What type of cleavage does the following reaction involve? i) ii)

15 A. i) homolytic; ii) homolytic B. i) heterolytic; ii) heterolytic C. i) homolytic; ii) heterolytic D. i) heterolytic; ii) homolytic 52. Why is entropy negative for ring closures? A. Closing a ring results in fewer molecules. B. Closing a ring results in more molecules. C. Closing a ring releases energy. D. Closing a ring restricts the rotation around individual carbon-carbon bonds 55. Which of the following is an energy diagram for a three step reaction? (B) 56. What is a transition state? A. An isolable intermediate in a reaction. B. The starting materials of the reaction. C. A local maximum on the energy diagram. D. A point between the starting materials and the product. 57. What is an intermediate? A. A point on the reaction pathway that has a discrete lifetime. B. A local maximum on the energy diagram. C. A point half-way between the starting materials and products. D. The highest energy compound on an energy diagram. 58. Identify the nucleophilic atom(s) in the following molecule? A. carbon at the right terminus B. oxygen C. nitrogen D. all of the above

16 E. both B and C 59. Which of the following cannot be a electrophile? 60. For the following reaction step, indicate which pattern it belongs to? A. Proton Transfer B. Loss of Leaving Group C. Nucleophilic Attack D. Rearrangement 61. For the following reaction step, indicate which pattern it belongs to? A. Proton Transfer B. Loss of Leaving Group C. Nucleophilic Attack D. Rearrangement 62. What is wrong with the following mechanism? A. There is no leaving group, so there should be no arrows. B. The arrow should be removing a proton from the H2 group. C. An arrow is also needed to indicate the loss of the leaving group. D. The arrow indicating the formation of the C- bond (nucleophilic attack) should start at the bromide anion. 63. Identify the sequence of steps in the following reaction.

17 A. Proton transfer, Proton transfer B. Proton transfer, Loss of leaving group C. Nucleophilic attack, Proton transfer D. Proton transfer, Nucleophilic attack 64. Identify the sequence of steps in the following reaction. A. Proton transfer, Proton transfer, Nucleophilic Attack B. Proton transfer, Nucleophilic attack, Proton transfer C. Nucleophilic attack, Proton transfer, Loss of leaving group D. Proton transfer, Loss of leaving group, Nucleophilic Attack 65. Which of the following is the correct IUPAC name of the following structure? A. 2-omo-3-butylpentane B. (2S)-omo-4,5-dimethylheptane C. 3,4-Dimethyl-6-bromoheptane D. 2-omo-4-methylhexane 66. How many primary carbons are there in the following compound?

18 F F F A) 1 B) 2 C) 3 D) 4 E) Which of the following is a reasonable definition of a concerted reaction? A. It is a reaction which takes place in a series of steps. B. It is a reaction which produces a loud noise. C. It is a reaction in which all bond-breaking and bond-forming occurs at the same time. D. It is a substitution reaction. 68. Which of the following is not a possible step in a substitution reaction? 69. Which of the following is the product of the following SN2 reaction?

19 70. Rank the following substrates from most to least reactive in an SN2 reaction. A. A>B>C>D B. D>C>B>A C. A>C>B>D D. D>C>B>A 71. Rank the following substrates from most to least reactive in an SN2 reaction. A. A>B>C>D B. C>D>B>A C. C>B>A>D D. D>C>B>A 72. Rank the following substrates from most to least reactive in an SN1 reaction. A. A>B>C>D B. A>B>D>C C. D>A>B>C D. D>C>B>A 73. Which of the following is the major product for the following SN1 reaction?

20 74. What type of solvent would be best for obtaining an optically active product in the following reaction? A. polar protic B. polar aprotic C. apolar aprotic D. water 75. Which of the following is the correct IUPAC name for the following compound? A. 2-ethyl-1,1,3-trimethylbutene B. 3-ethyl-2,4-dimethyl-2-pentene C. 2,4-dimethylhexene D. 4-ethyl-1,3-dimethyl-3-pentene 76. Which of the following is the correct IUPAC name for the following compound? A) (3S, 4Z)-3,4,5-trimethyl-4-heptene B) (3R, 4E)-3,4,5-trimethyl-4-heptene C) (3Z, 5S)-3,4,5-trimethyl-3-heptene D) (3E, 5R)-3,4,5-trimethyl-3-heptene E) none of the above 77. Is the following alkene?

21 A. E B. Z C. neither 78. Rank the following from most to least stable. A) A, B, C B) C, B, A C) B, C, A D) B, A, C 79. Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide? Cl Ph Ph Ph Cl Cl Cl A. B. C. D. Ph 80. What is the product of the following elimination?

22 A B C D E. none of these 81. Which of the following shows a mechanism for a concerted elimination? 82. What would be the best base for performing the following elimination? A. NaMe B. NaH C. NaH D. NatBu E. NaNH2 83. What is the product of the following elimination?

23 A B C D E 84. Which of the following alkyl halides would afford the indicated product upon reaction with sodium ethoxide? E. both C and D 85. What are the steps in the following mechanism in correct order? A) loss of leaving group, rearrangement, proton transfer B) concerted in one step: Proton transfer, loss of leaving group, proton transfer C) Proton transfer, loss of leaving group, rearrangement, proton transfer D) Proton transfer, loss of leaving group, proton transfer, rearrangement E) none of the above 86. Which of the following is the structure of the rearranged carbocation in the following dehydration? 87. The expected Markovnikov addition product of HI to 2-methyl-2-butene is:

24 A) 2-iodopentane B) 2-iodo-1-methylbutane C) 1-iodo-2-methylbutane D) 2-iodo-2-methylbutane E) 3-iodo-2-methylbutane 88. What is the expected major product for the following reaction? H RR? I A B II C III IV D V E 89. Which of the alkenes below would be expected to produce a chirality center upon hydrohalogenation in the presence of peroxide? A) B) C)

25 D) E) 90. Treatment of (S)-6-chloro-1-methyl-1-cyclohexene with H3 + is expected to produce which of the following? A) I and III B) II C) III and V D) IV E) I, III and V 91. What is the expected major product for the following reaction? A) B) C) D) E) 92. What is the expected major product for the following reaction sequence?

26 A) B) C) D) E) 93. What is the expected major product for the following reaction sequence? 1. BD 3 THF 2. H 2 2, NaH + enantiomer H D D H + enantiomer + enantiomer D H + enantiomer D + enantiomer A I II B C III IV D EV

27 94. What is the expected major product for the following reaction? 2, CH 3 H? H + enantiomer H 3 C + enantiomer CH 3 + enantiomer CH 3 + enantiomer H 3 C A B C D E 96. Treating 2-methyl-2-pentene with 2 is expected to produce which of the following as the major product? A) 2,3-dibromo-2-methylpentane B) 2,2-dibromo-2-methylpentane C) 3,3-dibromo-2-methylpentane D) 2-bromo-2-methylpentane E) 3-dibromo-2-methylpentane 97. The reaction of 2 with 1-methylcyclohexene, in the presence of ethylamine (EtNH2), is expected to produce which of the following as the major product? CH 3 NHEt + enantiomer CH 3 NHEt + enantiomer CH 3 NHEt + enantiomer CH 3 NHEt + enantiomer A B C D E I II III IV V NHEt

28 99. f the alkenes shown, which would produce the product shown below, upon treatment with ozone, followed by zinc metal and water?? H H H H H H H C C C C C C C H H H H H CH 3 CH 3 CH 3 A B C D E I II III IV V 100. What is the expected major product of the following reaction sequence? Cl 1. t-buk, t-buh 2. H A B C D E I II III IV V Cl 101. What is the expected major product of the following reaction sequence? A) B) C)

29 D) E) 102. For the following reaction sequence, which molecule is an expected major product? A) B) C) D) E) 103. Provide the systematic IUPAC name for (CH3)2CHC CCH2C(CH3)3. A) 1,1,5,5,5-Pentamethyl-2-pentyne B) 1,1,1,5,5-Pentamethyl-3-pentyne C) 2,2,6-trimethyl-4-heptyne D) 2,6,6-trimethyl-3-heptyne E) tert-butylisopropylacetylene 104. What is the correct IUPAC name for the molecule shown below? A) (E)-4-isopropyloct-3-en-5-yne B) (Z)-4-isopropyloct-3-en-5-yne C) (E)-5-isopropyloct-5-en-3-yne D) (Z)-5-isopropyloct-5-en-3-yne E) (E)-4-(2-methylethyl)oct-3-en-5-yne

30 105. Treatment of 2,2-dibromobutane with molten KH at 200 C would be expected to produce which of the following? A) (E)-2-bromo-2-butene B) (Z)-2-bromo-2-butyne C) 1,2-butadiene D) 1-butyne E) 2-butyne 106. What is the expected major organic product from treatment of 4-methyl-2-pentyne with hydrogen in the presence of Lindlar's catalyst? A) (E)-4-methyl-2-pentene B) (Z)-4-methyl-2-pentene C) (E)-2-methyl-2-pentene D) (Z)-2-methyl-2-pentene E) 2-methylpentane 107. What is the major expected product(s) of the reaction shown below? A) 2,2-Dichloropentane B) 3,3-Dichloropentane C) 2,3-Dichloropentane D) A and B E) B and C 108. Which of the following alkynes would give a single product under hydroborationoxidation conditions? A) 1-hexyne B) 2-hexyne C) 3-hexyne D) A and B would each give a single product E) A and C would each give a single product 109. Select the alkyne listed below that, upon treatment with ozone followed by water, would not produce carbon dioxide and a carboxylic acid as the final products? A) Ethyne

31 B) Propyne C) 1-Butyne D) 1-Pentyne E) 1-Hexyne 110. Which sequence of reactions is expected to produce cis-3-octene as the final, and major, organic product? A) I B) II C) III D) IV E) V 111. Which sequence of reactions is expected to produce the product below as the final, and major, organic product? A) 1) H2, Lindlar s cat.; 2) s4; 3) NaHS3/H2 B) 1) H2, Pt; 2) s4; 3) NaHS3/H2 C) 1) s4; 2) NaHS3/H2; 3) H2, Lindlar s cat. D) 1) Na, NH3(l); 2) s4; 3) NaHS3/H2 E) 1) s4; 2)NaHS3/H2; 3) Na, NH3(l)

Study Union: CHM 2210 Final Exam Review 1. The following molecules are related in what manner?

Study Union: CHM 2210 Final Exam Review 1. The following molecules are related in what manner? A) They are isotopes B) They are constitutional isomers C) They are the same structure D) They are composed