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.

21.An unknown alkyne with a molecular formula of give the following products upon ozonolysis. What is the structure of the starting material? (A) CH3CH2CH2C≡CCH2CH3 (B) (CH3)2CHC≡CCH2(CH3)2 (C) (CH3)2CHC≡CCH2CH3 (D) CH3CH2C≡CCH2CH3 (E) CH3CH2CH2C≡CCH2CH2CH3

22. Which of the following structures could be constructed by way of a malonate ester alkylation? (A)(B)(C)(D)(E) All of the above.

23.Rank the following molecules in order of increasing relative rate of SN1 solvolysis with methanol and heat (slowest to fastest reacting). (A) 3 ＜ 2 ＜ 4 ＜ 5 ＜ 1 (B) 2 ＜ 3 ＜ 4 ＜ 1 ＜ 5 (C) 5 ＜ 4 ＜ 3 ＜ 2 ＜ 1 (D) 2 ＜ 3 ＜ 4 ＜ 5 ＜ 1 (E) 1 ＜ 2 ＜ 5 ＜ 4 ＜ 3

24. Which of the following molecules, if isolated in its pure form, would demonstrate optical activity? (A) both IV and V (B) both I and III (C) only II (D) both III and IV (E) both I and V

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