課程名稱︰有機化學
課程性質︰
課程教師︰方俊民
開課學院：生農
開課系所︰農藝系 昆蟲系
考試日期（年月日）︰99/6/22
考試時限（分鐘）：110 mins
是否需發放獎勵金： 是
（如未明確表示，則不予發放）
試題 :
I.Simple choice(46%)There is only one correct answer in each question.
1.Which compound has the highest basicity? A. CH3CH2NH2 B. CH3CONH2
C. CH3C≡N D.C6H5NH2
2.Which is a secondary amine? A.benzylamine B.triethylamine C.N-methyl-
aniline D.2-nitroaniline
3.Which reagent reacts with aniline to give benzenediazonium chloride [C6
H5N≡N]+CL¯? A. NH4CL B. H2NNH2/HCL C. NaNO2/HCL D. NaNO3/HCL
4.Which compound shows IR absorption at 1710 cm¯1? A. acetone B.aniline
C. ethanol D. benzene
5.Which IR absorption is characteristic to alkyne compound? A. 3300cm¯1
B. 2100cm¯1 C.1710cm¯1 D. 1600cm¯1
6.The singlet appearing at δ 2.2 in the H-NMR spectrum of 30methoxy-2-bu-
tanone corresponds to: A. the 3-methoxy group B.the C-1 proton C.the C-
3 proton D. the C-4 proton
7.How many signals will appear in the 13C-NMR of p-dichlorobenzene? A. 1
B. 2 C. 3 D. 4
8.Which reageny can react with alkyl halide RBr to generate Grignard rea-
gent? A. Mg B.MgBr2 C. LiAlH4 D. LiOH
9.Which compound can react with Tollens' reagent?(AgNO3/NH4OH solution) to
form "silver mirror"? A.1-pentanol B.2-pentanone C.pentanal D.pentanoic
acid
10.Which compound is the strongest acid? A.acetic acid B.benzoic acid C.
trifluoroacetic acid D.4-methoxybenzoic acid
11.Which compound has the highest reactivity in hydrolysis? A.nitrile B.
ester C.amide D.acid chloride
12.An intramolecular amide is called A.lactam B.lactone C.lactose D.lactate
13.Acid-catalyzed hydrolysis of methyl benzoate C6H5COOCH3 with isotopically
labeled water H2O* will produce A.C6H5CO*(OH) B.C6H5CO(O*H) C.C6H5CO*(O*H)
D.CH3O*H
14.Which compound can undergo self-aldol reaction? A.formaldehyde B.benzalde-
hyde C.2-propen-1-al D.butanal
15.Which compound can be generated by heating C6H5COCH2COOH at 120。C? A.CO2
B.H2O C.acetic acid D.benzene
16.Which compound contains the most acidic α-H? A.CH3COOCH3 B.CH3CH2COOCH3
C.CH2(COOCH3)2 D.PhCH(COOCH3)2
17.Which compound can be obtained from the reaction of propanal in NaOD/D2O?
A.CD3CH2CHO B.CH3CD2CHO C.CH3CH2CDO D.CH3CH2CDDOH
18.Which is the tautomer of propanal? A.CH3COCH3 B.CH2=CHCH2OH C.CH3CH=
CH(OH) D.CH2=CH-OCH3
19.Which reagent reacts with methyl benzoate to give benzyl alcohol? A.NaBH4
B.LiAlH4 C.NaOH D.CrO3
20.Ziegler-Natta catalyst is used for preparation of A.polypropylene B.poly-
amide C.polyester D.polyurethane
21.Glycoside bonds are A.ester bonds B.amide bonds C.hydrogen bonds
D.acetal bonds
22.Peptide bonds are A.ester bonds B.amide bonds C.hydrogen bonds
D.acetal bonds
23.Which compound forms lipil bilayer in water? A fatty acid B.steroid C.tri
glyceride D.phospholid
II.(6%)Aldehyde forms acetal more readily than ketone. Give suitable reagents
and products(A),(B). and (C) to complete the following transformations.
Ｏ ／＼ ／＼
∥ O H+ O ∕ (B) O ∕H3O+
╱ ╲╱╲// + (A) → ╱╲╱╲/— O → ╱╲╱╲/—O → (C)
︳ ︳ ︳
H H H
III.(12%)The following are three methods for preparation of 1-phenylethanol
[C6H5CH(OH)CH3]. Show the structure formulas of A, B, C, D, E and F
(1)Reduction of acetophenone A with a reducing agent B.
(2)Addition reaction of benzaldehyde C with a Grignard reagent D.
(3)Addition reaction of acetaldehyde E with a Grignard reagent F.
IV.(8%)The following intramolecular reactions include:(1)Claison condensation,
(2)hemiacetal formation, (3)aldol reaction, (4)lactone formation. Draw the
structures of products.
V.(12%)The structure of adenosine diphosphate (ADP) is shown.
(1)Indicate the position of N-glycoside bond.
(2)Indicate the position of phosphoric ester.
(3)Indicate the position of phosphoric anhydride.
(4)Draw the structure of D-ribose as the α-anomer in furanoside form.
(5)Draw the structure of D-ribose in Fischer Projection.
(6)Assign the (R/S) notation to each of stereocenters in D-ribose.
VI.(10%) Outline a procedure for separating a mixture of aniline(C6H5NH2),
benzoic acid(C6H5COOH) and toluene(C6H5CH3) using acids(1M HCL), bases(1M
NaOH), and organic solvent (Et2O)
VII.(6%) The pKa values of the COOH and NH4+ groups in glycine(H2NCH2COOH) are
2.35 and 9.78, respectively.
(1)How the isoelectric point(PI=6.06) of glycine is derived?
(2)Show the major structure of glycine at PH = 6.06
(3)Show the structure of glycine-glycine ( a dipeptide).
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