36. Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?
(A)water + dilute acid
(B)water + concentrated acid
(C) oxymercuration-demercuration
(D) hydroboration-oxidation

32. Consider the constitutional isomers 2-methylbut-1-ene, 2-methylbut-2-ene, and 3-methylbut-1-ene. When each of these alkenes is subjected to catalytic hydrogenation (H2, Pt), a single product results. Which of the following best describes the structural relationship among these products? (A)The products are cis-trans isomers. (B)The products are identical. (C) The products are constitutional isomers.(D)The products are enantiomers.

33. Which of the following alkenes has the smallest molar heat of hydrogenation (ie, releases the least heat upon hydrogenation)? (A)2,3-dimethyl-2-butene (B)2-methyl-2-butene (C) trans-2-butene(D)cis-2-butene

34. HBr can be added to an alkene in the presence of peroxides (ROOR). What function does the peroxide serve in this reaction? (A)nucleophile (B)electrophile (C) radical chain initiator(D)acid catalyst

35. Provide the reagents necessary to complete the following transformation.(A)1. BH3∙THF 2. H2O2, HO- (B)H2O, H2SO4 (C) OsO4, H2O2(D)CH3CO3H

37. What is the correct IUPAC name for the following structure?(A)(Z) 4-methyl-3-hexen-1-thiol (B)(Z) 6-mercapto-3-methylhex-3-ene (C)( E ) 6-mercapto-3-methylhex-3-ene(D)( E ) 4-methylhex-3-en-1-thiol

38. The reaction of CH3CH2MgBr with CH3COCH2CH3 gives ________. (A)an achiral product (B)a mixture of diastereomers (C) the racemate of a chiral product(D)a single enantiomer

39. Which alcohol reacts most rapidly with the Lucas reagent? (A)benzyl alcohol (B)methanol (C) 2-propanol(D)isobutanol

40. Which of the following oxidants will convert a primary alcohol to an aldehyde?1) sodium dichromate /sulfuric acid 3)pyridinium chlorochromate2) copper oxide 4) dimethylsulfoxide, oxalyl chloride (A)3 & 4 (B)2, 3, & 4 (C) 3(D)1, 2, 3, & 4

41. What are the relative integrations for the 1H NMR signals for the following compound?(A)3:1:2:2 (B)3:3:2 (C) 3:1:4(D)5:3

42. If a molecule contains 4 elements of unsaturation and signals in the 1H NMR spectrum between δ 7.0 and 8.0 ppm, what structural group is likely to be present? (A)a carbonyl group (B)an aromatic ring (C) a hydroxyl group(D)a cyclohexyl ring