12. Select the major product in the following reaction:

(A)
(B)
(C)
(D)
(E)

13. Select the major product in the following two reactions: (A) (B) (C) (D) (E)

14. Select the correct IUPAC name for the following compound. (A) 2-bromo-3-ethyl-6-propyl-7-t-butylnonane (B) 2-bromo-3,7-diethyl-6-propyl-8,8-dimethylnonane (C) 2-bromo-3,7-diethyl-8,8-dimethyl-6-propylnonane (D) 8-bromo-2,2-dimethyl-3,7-diethyl-4-propylnonane (E) 8-bromo-3,7-diethyl-2,2-dimethyl-4-propylnonane

15. Select the major product in the following two reactions: (A) (B) (C) (D)(E)

16. Which of the following statements about the π molecular orbital description of cyclobutadiene is not correct? (A) Cyclobutadiene has two degenerate nonbonding π molecular orbitals. (B) Cyclobutadiene has a single bonding π molecular orbital. (C) Cyclobutadiene has two electrons in nonbonding π molecular orbitals. (D) Cyclobutadiene has one electron in an antibonding π molecular orbital which makes it antiaromatic. (E) none of the above

17. What is the best method for the preparation of p-chlorotoluene in high yield? (A) start with benzene; methylate; chlorinate (B) start with benzene; chlorinate; methylate (C) start with toluene; chlorinate (D) start with chlorobenzene; methylate (E) start with p-aminotoluene; NaNO₂/HCl, 0°C; CuCl

18. Predict the major organic product of the reaction between N-methylbenzamide and sodium propanoate in propyl alcohol at room temperature. (A) N-propylbenzamide (B) propyl benzoate (C) phenyl propanoate (D) benzoic propanoic anhydride (E) no reaction

19. Which of the following amines will react with cyclopentanone to form an enamine? (A) CH₃CH₂CH₂CH₂NH₂ (B) (CH₃)₃N (C) pyridine (D) (CH₃)₃CNH₂ (E) none of the above

20. Which of the following reagent will quantitatively convert an enolizable ketone to its enolate salt? (A) lithium hydroxide (B) lithium diisopropylamide (C) methyllithium (D) diethylamine (E) pyridine

21. Which of the following could result from the dehydration of an aldol? (A) 4-methyl-3-penten-2-one (B) 4-methyl-4-penten-2-one (C) 4-methyl-5-hexen-2-one (D) 4-methyl-4-hexen-2-one (E) 3-methyl-4-penten-2-one

22. Which of the following reagents would reduce carboxylic acids and esters into alcohols? (A) H₂/Raney Ni (B) 1. LiAlH₄ 2. H₃O⁺ (C) Na/NH₃ (D) 1. NaBH₄ 2. H₃O⁺ (E) Zn(Hg)/H⁺

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