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課程名稱︰有機化學丙
課程性質︰
課程教師︰何東英
開課系所︰化學系
考試時間︰2005 6 9
試題 :
1.Discuss the difference between Sn1 and Sn2 reactions in terms of solvent,
mechanism,kinetics,energy diagram,substrate effect,stereochemistry etc.
2.Give major product for the following reaction.
a.1-bromobutane + CH3CH2O-Na+ (ethanol) →
b.1-bromobutane + (CH3)3CO-Na+ (t-butyl alcohol) →
c.2-bromopropane + CH3CH2S-Na+ →
d.2-bromopropane + CH3CH2OH →
e.2-bromopropane +CH3CH2O-Na+ →
f.1-bromo-1-methylcyclohexane + CH3CH2O-Na+ (ethanol) →
g.1-bromo-1-methylcyclohexane + refluxing ethanol →
h.2-methyl-2-butanol + HCl →
i.2-phenylethanol +SOCl2 →
j.2-cyclohexylethanol + PCC →
k.1-pentanol + Na →
l.1-octanol + HBr + ZnBr2 →
m.1-methylcyclopentanol + H2SO4 (heat) →
n.cyclopentanol + PBr3 →
o.1-pentanol + CrO3 , H+ →
p.ethylene oxide + H2O (H+) →
q.cyclohexene + m-chloroperbenzoic acid →
r.2-methylpropene +CH3OH (H+) →
s.CH3CH2OCH(CH3)2 + HI (heat) → two products
t.C6H5OCH3 + BBr3 (heat) (H2O) → two products
3.Give correct synthesis for the following
a.from bromobenzene and ethylene oxide to 2-phenylethanol
b.from propyne and ethylene oxide to 3-pentyne-1-ol
c.Williamson method for the synthesis of CH3OC(CH3)3
d.from 1-butyne to 3-hexyne
e.from propanol to propyl cyanide
4.Explain why 1-butanol reacts with hydrogen halides in the rate order
HI > HBr > HCl (to from in each case the corresponding butyl halides)
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