臺北醫學大學104學年度碩士班暨碩士在職專班招生入學考試_有機化學試題

臺北醫學大學 104 學年度碩士班暨碩士在職專班招生入學考試

1. Triethylamine (TEA) is a stronger base than

Ⓐ CH3COONa Ⓑ t-BuOK Ⓒ NaOH Ⓓ pyridine

2. Cyclohexane prefers the

Ⓐ boat form Ⓑ twist form Ⓒ chair form Ⓓ none of the above

3. Which of the following molecules is chiral?

Ⓐ 1,2-pentadiene Ⓑ 2,3-pentadiene

Ⓒ 2-methyl-2,3-pentadiene Ⓓ 2-chloro-4-methyl-2,3-pentadiene

4. In the proton NMR, what region of the spectrum does typically indicate the hydrogens bound to the aromatic ring?

Ⓐ 9.0-10.0 ppm Ⓑ 7.0-8.0 ppm Ⓒ 4.5-5.5 ppm Ⓓ 2.0-3.0 ppm

5. If a signal is observed in the range of 170 to 200 ppm in a C-13 NMR spectrum, what is the most likely type of functional group associated with that carbon atom?

Ⓐ carbon/carbon double bond Ⓑ carbonyl carbon

Ⓒ aromatic carbon Ⓓ carbon/carbon triple bond

6. About pKa of carboxylic acid A, B, C and D, which of the following statements is correct?

Ⓐ D<A<C<B Ⓑ B<C<D<A Ⓒ A<D<C<B Ⓓ B<C<A<D

7. What type of carbon environment does not generate a signal in the DEPT-90 spectrum and give a negative signal in the DEPT-135 spectrum?

Ⓐ carbonyl Ⓑ methane Ⓒ methylene Ⓓ methyl

8. The structure of D-arabinose is shown below. Which of the following statements correctly describes the configurations of the asymmetric carbons in D-arabinose?

Ⓐ 2S, 3R, 4R Ⓑ 2R, 3S, 4S Ⓒ 2S, 3R, 4S Ⓓ 2R, 3S, 4R

9. Which of the following statements correctly describes the structural relationship between D-gulose and L-gulose? Ⓐ diastereomers and epimers Ⓑ diastereomers but not epimers

臺北醫學大學 104 學年度碩士班暨碩士在職專班招生入學考試

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10. Amino acids have:

Ⓐ high melting points and low solubility in water.

Ⓑ large dipole moments and are more acidic than most carboxylic acids. Ⓒ high melting points and large dipole moments.

Ⓓ low solubility in water and small dipole moments. 11. What is the structure of compound C.

O OEt LAH A (COCl)₂, DMSO B PPh3 C Ⓐ O H Ⓑ H Ⓒ Cl O Ⓓ H

12. Please assign the correct chirality of the structure.

H3C

CH3

CH3

H₃C

Ⓐ 2R,6R Ⓑ 3R,7R Ⓒ 3S,7R Ⓓ 4R,8R

13. Please select the major products A and B under the corresponding reaction conditions.

H3C CH3 CH3 (1) BH3, THF (2) H2O2, -OH (1) Hg(OAc)2, CH3OH (2) NaBH4 Compound A Compound B Ⓐ H₃C CH₃ CH3 _H 3C CH3 CH3 A: B: OH OH Ⓑ H3C CH3 CH3 _H 3C CH3 CH3 A: B: OH OH Ⓒ H3C CH₃ CH₃ H₃C CH3 CH3 A: B: OH OH Ⓓ H3C CH₃ CH₃ H₃C CH3 CH3 A: B: OH OH

14. Please choose the correct sequence of reactivity of following carboxylic acid derivatives.

R Cl O R OR' O R NHR' O R O O R' O A: B: C: D: Ⓐ A > B > C > D Ⓑ C > A > B> D Ⓒ A > C > B > D Ⓓ C > A > D > B 15. Which of the following substituted benzoic acids is the most acidic?

OH O OH O OH O OH O H Cl H3C O2N A: B: C: D: Ⓐ A Ⓑ B Ⓒ C Ⓓ D

16. Which of the following reagents could react with acid halide to afford a ketone?

Ⓐ (CH3CH2)2CuLi Ⓑ NaBH4 Ⓒ LiAlH4 Ⓓ RMgBr

17. Which of the following amines could be prepared by Gabriel amine synthesis? Ⓐ 10

amine Ⓑ 20 amine Ⓒ 30 amine Ⓓ 40 amine

18. What is the name of the following reaction? Ar N N Cl

CuX

Ar X + N₂

Ⓐ Sonogashira reaction Ⓑ Suzuki reaction Ⓒ Sandmeyer reaction Ⓓ Stille reaction 19. Which of the following amino acids contains an imidazole ring?

Ⓐ proline Ⓑ arginine Ⓒ tryptophan Ⓓ histidine

臺北醫學大學 104 學年度碩士班暨碩士在職專班招生入學考試

5. Please draw the plausible mechanism of the following reaction. H₃O+, heat

O O

OCH₃

O

6. Please draw the plausible mechanism of the following reaction.

CH3OH, heat

Br

7. Please provide a reasonable synthetic route and appropriate reagents to prepare compound B from compound A.

8. Please predict the correct structure and write down your reasons. Ⓐ Elemental analysis: C, 61.22%; H, 6.16%; O, 32.62%.

Ⓑ Molecular Weight: 196 g/mole Ⓒ 13 C-NMR & 1H-NMR spectra: OH O OH O A B

臺北醫學大學 104 學年度碩士班暨碩士在職專班招生入學考試

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