10. A three-carbon, nitrogen-containing compound exhibits three NMR peaks (d 11.2, 27.3, and 44.9). Which of the following compounds best matches this spectral data?
(A) H₂NCH₂CH₂CH₂OH
(B) (CH₃)₂CHNH₂
(C) CH₃NHCH₂CH₃
(D) CH₃CH₂CH₂NH₂
(E) CH₃CH₂C≡N

11.The following substrate is a starting material in the synthesis of compounds having opiod activity (J. Med. Chem. 2011, 957). Which product that would NOT result from the reaction below. (A)(B) (C)(D)(E) All products that result from the reaction

12. What would be the product of the following reaction? (A)(B)(C)(D)(E)

13.Why do acetal-forming reactions that use ethylene glycol (HOCH2CH2OH) have more favorable equilibrium constants than those using methanol? (A) Ethylene glycol reacts more rapidly. (B) They are more favorable on entropy grounds. (C) They are more favorable on enthalpy grounds. (D) Ethylene glycol is acidic and catalyzes the reaction. (E) The ethylene acetal can serve as a protecting group.

14. The reagent which converts a carbonyl group of a ketone into a methylene group is (A) Na, NH3, CH3CH2OH (B) LiAlH4 (C) NaBH4, CH3CH2OH (D) Zn(Hg), conc. HCl (E) LiAlH[OC(CH3)3]3

15. Which sequence correctly ranks the following aromatic rings in order of increasing rate of reactivity with chlorine and aluminum chloride?  (A) 1 ＜ 2 ＜ 3 (B) 2 ＜ 3 ＜ 1 (C) 3 ＜ 2 ＜ 1 (D) 2 ＜ 1 ＜ 3 (E) 1 ＜ 3 ＜ 2

16.In electrophilic aromatic substitution reactions the hydroxyl group is an o,p-director because _____. (A) it donates electron density to the ring by induction and destabilizes the meta sigma complex (B) it donates electron density to the ring by resonance and stabilizes the ortho and para sigma complexes (C) it donates electron density to the ring by induction and stabilizes the ortho and para sigma complexes (D) it donates electron density to the ring by resonance and destabilizes the meta sigma complex (E) it withdraws electron density from the ring by induction and destabilizes the meta sigma complex

17.Which compounds in the following are not aromatic? (A) a, b, c (B) d, f, g (C) c, f, h (D) d, e, h (E) a, g, h 

18. When 1 mole of anhydrous HCl is reacted with excess 1,3-pentadiene, both the 1,2 and the 1,4-addition products are formed. Which of the following structures shown below is the     least likely     to be one of these products? (Note: When a chiral carbon is formed in this reaction a racemic mixture results, only one of the two possible enantiomers is shown.) (A)(B) (C)(D)(E)

19.When 2-ethylcyclohexanone is treated with catalytic base in excess D2O, how many deuterium atoms become incorporated in the organic compound? (A) 0 (B) 1 (C) 2 (D) 3 (E) 5

20. In the formation of the following ether, which reaction is preferred and why? (A) Reaction B is preferred because the oxidation step works best for primary alcohols. (B) Reaction A is preferred over reaction B because the smaller methyl iodide would make a better nucleophilic target. (C) Reaction A is preferred because the the formation of the carbocation would be stabilized in the benzylic position. (D) Reaction B would be preferred because Iodine is a better leaving group for the SN1 reaction. (E) There is no difference in these two reactions they would give approximately the same yields.

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