33. Choose the reactants and reagents that would produce 1-butene as the major product.

(A) (a) + (b)
(B) (b)
(C) (a)
(D) (c)
(E) (a) + (c)

34. Normally, heating an initial aldol product (the β-hydroxyaldehyde) causes dehydration. However, heating the compound below with base does not cause dehydration, but rather, decomposition to form 2-ethylbutanal. This is because: (A) There are no protons β to the carbonyl. (B) There are no protons adjacent to the OH, and the dehydration reaction requires E1 conditions. (C) There are no protons α to the carbonyl, and aldol condensations are reversible. (D) Heating any organic compound above room temperature causes decomposition. (E) None of these is true.

35. Choose the correct statement given the following information:(A) Fe2+(aq) is more likely to be oxidized than Fe2+ complexed to CN-.(B) Fe3+(aq) is more likely to be reduced than Fe3+ complexed to CN-.(C) Both A and B are true.(D) Complexation of Fe ion with CN-has no effect on their tendencies to become oxidized or reduced.(E) None of these is true.

36. Which of the following additions to 2-methylpropene occurs with anti-Markovnikov orientation?(A) Catalytic hydrogenation (H2/Pt) (B) Addition of HOBr (C) Addition of HI(D) Addition of HBr in the presence of ROOR (E) Oxymercuration-Demercuration

37. Which of the following alcohols will react most rapidly with the Lucas reagent?(A) (CH3)3COH (B) CH3CH2CH2CH2OH (C) CH3CH(OH)CH2CH3(D) (CH3)2CHCH2OH (E) (CH3)3CCH2OH

38. Which of the following dienes would undergo a Diels-Alder reaction?(A) 3-methylenecyclohexene (B) 3-methyl-1,4-cyclohexadiene (C) 2-methyl-1,3-cyclohexadiene(D) 1,4-cyclohexadiene (E) 4-methylenecyclohexene

39. Which of the following is the strongest acid?(A) 1-pentene (B) 2-pentene (C) 1,4-pentadiene (D) cyclopentadiene (E) cycloheptatriene

40. The correct decreasing order of reactivity with X+is(A) IV＞III＞II＞I (B) II＞IV＞III＞I (C) III＞I＞IV＞II (D) II＞IV＞I＞III (E) III＞I＞II＞IV

41. Which compound would be expected to show intense IR absorption at 1780 cm-1？(A)(B)(C)(D)(E)

42. Which compound would be expected to show an intense peak in the mass spectrum at m/z 58？(A) CH3C(O)CH2CH2CH3 (B) CH3CH2C(O)CH2CH3 (C) (CH3)3CCHO(D) (CH3)2CHC(O)CH3 (E) (CH3)2CHCH2CHO

43. The acid which could not be prepared by the reaction of an organic halide with cyanide ion followed by acid hydrolysis of the nitrite.(A) CH3CH2CO2H (B) PhCH2CO2H (C) (CH3)3CCO2H(D)(E)

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