15. Which of the following is aromatic?
(A) cycloheptatrienyl cation
(B) 1,3,5-hexatriene
(C) cyclobutenyl anion
(D) 1,3-cyclohexadiene
(E) cyclopentadienyl cation

16.How many hydrogens in the structure of 2,3-dimethylcyclopentanone are replaced by deuteriums when it is shaken in D2O containing trace hydroxide?(A) 1 (B) 2 (C) 3 (D) 6 (E) 7

17. Consider molecules with the formula C10H14Br2O2. Which of the following structural features is possible within this set ofmolecules?(A) 3 triple bonds(D) 4 double bonds(B) 2 rings and 1 double bond(E) 3 rings and 2 double bonds(C) 2 rings and 1 triple bond

18. Predict the two most likely mechanisms for the reaction of 2-iodohexane with sodium ethoxide.(A)SN2 and SN1 (B) E1 and E2 (C) SN2 and E2(D) E1 and SN1 (E) E2 and SN1

19. When 1,3-butadiene reacts with CH2=CHCN, which of the terms below best describes the product mixture?(A) a mixture of two diastereomers(C) a racemic mixture(E) a mixture of bicyclic compounds(B) a single compound(D) optically active

20. Give the product for the following reaction.(A) alanine(B) leucine (C) valine(D) isoleucine(E) glycine

21. Which of the following statements correctly describes the contribution of △S° to△G°?(A) The entropy term makes a greater contribution to AG° at high temperatures.(B) The entropy term makes a greater contribution to AG° at low temperatures.(C) The entropy term makes a greater contribution to AG° in exothermic reactions.(D) The entropy term makes a greater contribution to AG° in endothermic reactions.(E) The entropy term always makes a more significant contribution to AG° than does the enthalpy term.

22. What compound is produced when N,N-dimethylpropanamide is treated with LiAlH4?(A) CH3CH2CONH₂ (B) CH3CH2CH2NH2(C) CH3CH2CH2OH(D) CH3CH2CH2N(CH3)2 (E) CH3CH2N(CH3)2

23. Which ofthe following is a vicinal dihalide?(A) cis-1,2-dibromocyclopentane(B) 3,3-dichloropentane(C) trans-1,4-diiodocyclohexane(D) isobutyl chloride(E) 1,3-dibromoheptane

24. Reduction of a 2-ketohexose with NaBH4 yields:(A) a single aldohexose (B) a mixture of acetals (C) a mixture of alditols(D) a mixture of pyranoses (E) a mixture of cyclic hemiacetals

25. When the 1,7-diester CH3O2CCH2CH2CH(CH3)CH2CH2CO2CH3 is treated with sodium methoxide and the reaction mixture issubsequently neutralized with acid, what kind of compound is the major organic product?(A) a cyclic ẞ-diketone (B) a cyclic ẞ-ketoester (C) an acyclic ẞ-diester(D) an acyclic ẞ-ketoacid (E) a cyclic ẞ-diketone

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