課程名稱︰有機化學二
課程性質︰必修
課程教師︰羅禮強
開課系所︰化學系
考試時間︰April 6 2006
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試題 :
1.Please proveid structure for all the intermediates and describe the type
of mechanism by which each is formed.(9 point)
CL2 NaOH CL2 Ca(OH)2
CH2=CHCH3 ─→ A(C3H5CL) ─→ B(C3H6O) —→ C(C3H7CLO6) ──→ D(C3H6O2)
heat H2O H2O heat
HCL
─→1,2,3-Propanetriol
H2O
2.When (S)-3-phenyl-2-butanone is left standing in aqueous acid,it slowly
loses its optical activity.Please explain this obsevation.(5 point)
3.Please propose a mechanism for the following transformation.(6 point)
O
O BF3 ∥
﹨╱ ╲／ ──→ ╲╱╲
/￣￣ \ ╱\
4.Please propose a mechanism for the following transformation.(6 point)
OH O
╱╲╱ ∥ ／＼／ ＼ ／
｜ ｜ + ╱╲ HBr ｜ ｜ > +CH3OH
╲／＼ OCH3 ──→ ╲／＼ ／ ＼
OH O
5.What are crown ether ? Please describe how to make "purple benzene".(6 point)
6.Please propose a mechanism for each step in this transformation and account
for the regopselectivity of HCL addition.(8 point)
O Cl O
╲／∥ ╲|／∥ OH
\\╱╲ HCL \\／＼ i)NaOH ╲//＼／╲╱╲／
｜ ∣﹍CH3 ─→ ｜ ｜﹍CH3 ──→ ｜ ︴ ∥
╲／ ╲／ ii)HCL O
7.There are three methyl groups on 3-methyl-2-butanol shown below.Please
indicate the relationship between a-c and a-b methyl groups.(4 point)
OH
｜
(a) ╲／╲ (c)
｜
(b)
8.Starting with cyclopentanone,show how to prepare these compounds.You may use
any other organic and inorganic reagent as necessary.(8 point)
(a)cis-1,2-Cyclopentanediol
(b)1-phenylcyclopentene
(c)Cyclopentene oxide
(d)trans-1,2-Cyclopentanediol
9.2,3-Diphenyloxirane could be prepared from the following reactions.
O
MCPBA / \
PhCH=CHPh ────→PhHC-CHPh
O
i)CL2,H2O / \
PhCH=CHPh ────→PhHC-CHPh
ii)CH3OHa
Suppose that the starting alkene is cis-1,2-diphenylethelene.
(a)What is the configuration of the epoxide formed in each sequence.
(b)Is the epoxide formed in either sequence optically active?Please explain
your answers.(8 point)
10.Deduce the structure of each of the following compounds on the basis of
their NMR spectra and molecular formulas.(20 point)
(a)C10H14 ;1H-NMR δ1.3(singlet,9H),7.0-7.5(multiplet,5H).
(b)C4H6CL2;1H-NMR δ2.2(singlet,3H),δ4.1(doublet,2H),δ5.7(triplet,1H).
(c)C4H10 ;13C-NMR δ18.9(CH3,two carbons),δ30.8(CH,one carbos)
,δ69.4(CH2,one carbon).
(d)C7H14O2;13C-NMR δ171.2(CH,one carbon),δ63.1(CH2,one carbos)
,δ37.2(CH2,one carbon),δ25.1(CH,one carbon)
,δ24.52(CH3,one carbon),δ21.0(CH3,two carbons).
11.When compound A(C5H12O) is treated with HBr,it forms compound B(C5H11Br).
The 1H-NMR spectrum of compound A has one singlet(1H),two doublet(3H,6H),
and two multiplets(both 1H).The H-NMR spectrum of compound B has a singlet
(6H),a triplet(3H), and a quartet(2H).Please identify compounds A and B.
(10 point)
12.Please provide a synthesis for the target molecule shown below.You may use
halobenzens and any other organic compounds no more than two carbon atoms
as your starting materials.(10 point)
OH
｜
／╲╱╲╱╲ ꈊ ∣O ｜
╲／
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