推 SummerWind86:強者,好利害的圖 06/22 21:23
課程名稱︰有機化學
課程性質︰必修
課程教師︰方俊民
開課系所︰醫技系、園藝系
考試時間︰2006/6/22 10:20~12:10
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試題 :
Ⅰ.Simple choice (48%). There is only one correct answer in each question.
1. Which compound has the highest solubility in water?
(A) 1-hexanol (B) 2-hexanol (C) 3-hexanol (D) 1,2-hexanediol
2. "Alkaloids" are reffered to the naturally occurring
(A) alcohols (B) aldehydes (C) acids (D) amines
3. The reaction of 1-pentanol with pyridinium chlorochromate (PCC) in CH2Cl2
solution will give
(A) 1-pentene (B) pentanal (C) 1-chloropentane (D) pentanoic acid
4. Which reagent is used to convert butanoic acid to butanoyl chloride?
(A) Cl2 (B) SOCl2 (C) HClO3 (D) HClO4
5. Which reaction is the best preparation of tert-butyl methyl ether?
(A) (CH3)3CO^-K^+ with CH3I (B) (CH3)3CO^-K^+ with CH3OH
(C) CH3O^-Na^+ with (CH3)3CCl (D) CH3O^-Na+ with (CH3)COH
6. Which compound has the highest acidity?
(A) 4-methylphenol (B) 4-nitrophenol (C) 4-methylcyclohexanol
(D) 4-nitrocyclohexanol
7. The correct IUPAC name for the molecule CH3COCH2CH2CH2COCH2CH3 is
(A) 2,6-octanedione (B) 3,7-octanedione (C) 2,6-octanediketone
(D) 3,7-octanediketone.
8. Which compound is the most reactive toward saponification with aqueous NaOH?
(A) CH3CO2CH3 (B) CH3CO2C(CH3)3 (C) CH3CONH2 (D) CH3CONHCH3
9. The correct IUPAC name for the molecule (CH3)2CHCH2CH2CN is
(A) 3-methylbutanenitrile (B) 3-methylbutylcyanide
(C) 4-methylpentanenitrile (D) 4-methylpentylcyanide
10.How many acidic hydrogens in CH3CH2CH2CO2H can be exchanged with deuterium
under alkaline conditions with NaOD inD2O?
(A) 1 (B) 3 (C) 5 (D) 8
11.Which compound is the most basic?
(A) triethylamine (B) aniline (C) pyridine (D) benzamide
12.Which compound belongs to secondary amine?
(A) 1-methylpropylamine (B) 2-methylpropylamine (C) N-methylpropylamine
(D) N,N-dimethylpropylamine
13.Reaction of CH2=CH-CH2CH2CHO with AgNO3 in aqueous ammonia (Tollens'
reagent) will give
(A) OHCH2CH2CH2CHO (B) CH2=CHCH2CH2CH=NH (C) H2C-CH(NH2)CH2CH2CHO
(D) CH2=CHCH2CH2CO2H
14.Treatment of ester CH3CO2CH3 with CH3ONa in CH3OH will give
(A) CH3CH(OCH3)2 (B) CH3C(OCH3)3 (C) CH3CH(OH)CH2CO2CH3
(D) CH3COCH2CO2CH3
15.Which compound might show a strong infrared absorption at 1715 cm^-1?
(A) cyclohexanone (B) hexanol (C) benzonitrile (D) nitrobenzene
16.How many proton signals will 1,3-dichlorobenzene (C6H4Cl2) show in its
^1H NMR spectrum? (A) 1 (B) 2 (C) 3 (D) 4
17.In the ^1H NMR spectrum of ethyl acetate CH3CO2CH2CH3, he CH2 signal will
appear as (A) singlet (B) doublet (C) triplet (D) quartet
18."Glycosides" are reffered to which functional group in carbohydrate
derivatives? (A) alcohol (B) acetal (C) ether (D) acid
19.The D-configuration in D-glucose is reffered to which chirality?
(A) 2R (B) 2S (C) 5R (D) 5S
20.Which is the major form of glucose is aqueous solution?
(A) α-glucofuranose (B)β-glucofuranose
(C) α-glucopyranose (D)β-glucopyranose
21.Peptide bonds are (A) easter bonds (B) amide bonds (C) hydrogen bonds
(D) acetal bonds
22.The isoelectric point of glycine is 5.97. Which form will predominate at
pH 3.0 in solution?
(A) H3N^+CH2CO2H (B) H2NCH2CO2H (C) H3N^+CH2CO2^- (D) H2NCH2CO2^-
23.The structure of "fat" belong to (A) fatty acid (B) phospholipid
(C) triacylglycerol (D) steroid
24.Which component is not essential in a nucleotide?
(A) amine base (B) sugar (C) carboxylate (D) phosphate
Ⅱ. (10%) There are four alcohols and three ethers having the molecular
formula C4H10O. Two of them are 1-butanol (CH3CH2CH2OH) and diethyl ether
(CH3CH2OCH2CH3).
1. Show the structures of other three alcohols, and classify them into
primary, secondary and tertiary alcohols.
2. Show the structures of other two ethers, and give their IUPAC names.
Ⅲ. (6%) The reduction of benzaldehyde (C6H5CHO) with NaBH4 in EtOH gives
benzyl alcohol (C6H5CH2OH).
1. Write the reaction mechanism.
2. What is the nucleophile?
3. What is the minimun amount of NaBH4 required for reduction of 1 mole of
benzaldehyde?
Ⅳ. (6%) Benzoic acid was subjected to the acid-catalyzed Fischer esterfication
with radioactive-oxygen (O*) labeled methanol CH3O*H, giving the products
of methyl benzoate and water. Show the reaction mechanism and whereabouts
of the radioactive-oxygen.
Ⅴ. (6%) When cis-2,4-dimethylcyclohexanone is treated with EtONa in EtOH for
1 day. A mixture of cis- and trans-2,4-dimethylcyclohexanone is obtained.
1. Write the reaction mechanism to account for the conversion of
cis-2,4-dimethylcyclohexanone to its trans isomer.
2. Which isomer is the major component when the reaction reaches equilibrium.
3. If one treats trans-2,4-dimethycyclohexanone with EtONa in EtOH, What
can happen?
Ⅵ. (24%) Give the missing reagents and structures, including stereochemistry
in appropriate cases, to complete the following reactions.
(1) ／＼ (A) ／＼ H3O^+
∣ ∥ ————→∣ ∣>O ————→ (B) C6H12O2
＼／ ＼／
(2) ／／＼ (C) ／／＼ i)LiAlH4, Et2O
∣ ∥ Br ————→∣ ∥ CN ———————→ (D) C6H11N
＼＼／＼／ ＼＼／＼／ ii) H2O
∣
∣(E)
↓
／／＼ O NH3, H2/Ni
∣ ∥ ∥ ——————→ (F) C9H13N
＼＼／＼／＼CH3
(3) Br i) Mg, Et2O
／／＼／ ii) CH3CHO
∣ ∥ ————————→ (G) C6H10O
＼＼／ iii) H2O
(4) O
∥
／／＼／＼ cat. ^-OH cat. H^+
∣ ∥ CH3 ————→ (H) C16H16O2 ————→ (I) C16H14O
＼＼／ heat
(5)
／／＼／＼CO2CH3 CH3ONa
∣ ∥ ————→ (J) C16H14O
＼＼／＼／CO2CH3 CH3OH
(6) CO2Et
∣ (K) ／／＼ CO2Et
／∣＼CO2Et ————→∣ ∥ ∣ H3O^+
H H ＼＼／＼／∣＼CO2Et ————→ (L) C9H10O2
H heat
注: ／／＼ 是苯環
∣ ∥
＼＼／
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