2002/11/21
Total:117
I)Simple choice(only one correct answer for each question):4%*12=48%
1)Rank in order of increasing acidity of the following compounds:
A:2,4,6-trinitrophenol; B:1-Propyne; C:(CH3)3NHCl; D:O2NCH2CH2OH
(A)A>B>C>D (B)B>A>C>D (C)B>C>A>D (D)A>C>D>B
2)Which of the following statement is CORRECT?
(A)Compound 5,8-bis(1-methylethyl)dodecane has 2 tertiary Hydrogens
(B)Compound 4-(1-ethylpropyl)-2,3,5-trimethylnonane has 5 tertiary Hydrogens
(C)Compound 2,6,6-trimethylbicyclo[3,1,1]hepta-2-ene has 3 secondary
Hydrogens
(D)The most stable structure of 2,3,4,6-tetrachloro-1-tert-butylcyclohexane
shown below has 2 chlorine atoms at the equatorial positions
(有附圖)
3)about Newman projection (圖略)
4)Which of the following could not be a resonance structure of CH3NO2?
(A) ‥- (B) ‥- (C) (D) ‥-
H :Ｏ: H :Ｏ: H H Ｏ:
| +╱.. | 2+╱..- | + .. | +╱‥
H─C─N═Ｏ H─C─N─Ｏ: H─C─N═Ｏ H─C═N
| ‥ | ‥ | ╲‥ - ╲‥
H H H :Ｏ: Ｏ─H
5)A split peak for the IR absorption due to bond streching is observed for the
carbonyl group in which of these compounds?
(A) O (B) O (C) O (D) O O
║ ║ ║ ║ ║
CH C─OH CH C─CH CH CH C─NH CH C─O─CCH
3 3 2 3 3 2 3 3
6)Rank in order of increasing vibration frequency of the following stretchings
in the frame
R O CH
╲ ∥ ∣3
R—C≡N C═O R—C—NH R—N—H
╱ 2
I R II III IV
(A)I>III>IV>II (B)IV>I>II>III (C)II>III>I>IV (D)III>II>I>IV
7)Quantify the difference in stability of the two structures shown below
CH
｜ 3
∕╲／—CH ∕╲／
H C—╱╲∕ 3 H C—╱╲∕
3 3
I II
(A)I is more stable than II by 7.5 KJ/mol
(B)I is more stable than II by 15 KJ/mol
(C)II is more stable than I by 7.5 KJ/mol
(D)II is more stable than I by 15 KJ/mol
8)How many stereocenters are there in the anabolic steroid methenolone?
(圖略) (A)4 (B)5 (C)6 (D) 7
25 。
9)What can be said with certainty if a compound has [α]D = -9.25
(A)The compound has the (S) configuration
(B)The compound has the (R) configuration
(C)The compound has no plane of symmetry
(D)The compound has an optical purity of less than 100%
10)about (S) config. selected (略)
11)Which is the best sequence to prepare 5-methyl-2-hexyne?
(A) CH3 (B)
| CH3
NaOH BrCH2CHCH3 | NaNH2 CH3Br
H3C-C≡CH ──→─────→ HC≡CCH2CHCH3 ──→──→
(C) CH3 (D)
| CH3
NaNH2 BrCH2CHCH3 | MeONa CH3Br
H3C-C≡CH ──→─────→ HC≡CCH2CHCH3 ──→──→
12)Which statement is true?
(A)butane and cyclobutane are consitional isomers
(B)E-1,2-dichloropropene and trans-1,2-dichloropropene are different
compounds
(C)ethane contains numerous conformational isomers including eclipsed and
staggered forms
(D)The chair conformational isomer of cis-1,2-dichlorocyclohexane must
display two chlorine atoms at equatorial position
II)By viewing from C2-C3 axis, draw Newman projections for the two eclipsed
and staggered conformational isomers of 2-methylbutane. Indicate the one
has the highest energy and the one has the lowest energy. (8%)
III)Please draw the following orbitals (5%*2=10%)
(A)σ bonding & σ* (B)π bonding & π*
IV)Allene, H2C=C=CH2, is somewhat unusual in that it has two adjacent double
bonds. Draw a picture showing the p orbitals involved in the π bonds of
allene(please indicate the p orbital axis). Is the central carbon atom
sp2- or sp-hybridized? (6%)
V)Sodium bicarbonate, NaHCO3, is the sodium salt of carbonic acid(H2CO3), pKa
=6.4. Which of the following substances will react with sodium bicarbonate?
(5%) __
O O O // \\__OH O
║ ║ ║ ﹨ ∕ ║
H3C-C-CH3 H3C-C-CH2-C-CH3 ═ H3C-C-OH
Acetone,pKa=19 2,4-pentanedione,pKa=9 Phenol,pKa=9.9 Acetic acid,pKa=4.5
VI)Please write three kinds of intermolecular interations and explain how
they can affect physical properties of molecules. (9%)
VII)Please explain the following terms (4%*4=16%)
(A)Frontier Orbitals (B)Protic solvent (C)Leveling effect (D)Lewis Acid
VIII)Draw strustures of the following compounds: (3%*5=15%)
(A)1-bromospiro[4.5]decane (B)sec-butanol (C)Trans-bicyclo[4.3.0]nonane
(D)tert-butylcyclohexane in chair form (E)(R)-1-bromo-2-butanol
選擇題解答:DBCDD BADC(CorD) BC
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※ 編輯: japwoon 來自: 61.229.202.118 (11/20 16:18)