[考試] 有機考古題...(醫技系的, 方俊民出的)

[frankieeeee (曙光女神之寬恕)]

: 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)COH6.

: 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) acid19.

: 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) phosphateⅡ.

: (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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→ frankieeeee:有些笨蛋為了搶第1000篇  所以把之前的弄飛了
→ frankieeeee:所以我為了大家  只好將就一下  再用出來好了 ~.~
推 forthday:我猜你就是那個笨蛋= =
推 orange90897:樓上正姐
推 forthday:大哥...你也選個字吧~~~這樣人家誤會很深=.=
推 forthday:97:樓上正解
推 lavender911:樓上正妹
推 orange90897:難道..難道仙女姐姐就不算正姐了嗎? 哭哭Q_Q
推 Inck:...........突然覺得看完這幾篇的自己很蠢.........Orz
推 frankieeeee:有誰可以提供正確解答阿...我頭很暈  @@
推 worldsky:看了這篇，感想...他很注重反應...大家一定要看...꘠
→ worldsky:至於範圍和難度都不離他說的範圍..看熟我想至少會及格
→ worldsky:希望可以順利拿到及格...小小心願而已...希望上天憐憫
推 forthday:1.D  2.D  3.??  4.B  5.A
推 frankieeeee:3 我做出來是B
推 orange90897:許我個清靜的暑假吧...聖光保佑