세종대 유기화학 2023-2 중간 기출문제 (정답 포함)

1. Which atom is described by the electron configuration 1s² 2s² 2p⁶ 3s² 3p¹?

2. Which of the atoms that are marked with an arrow are sp²-hybridized?

3. Which of these molecules are polar?

4. Which of the three molecules testosterone, methadone and hydrocodone contains a hydroxyl group?

5. Which equilibria lie considerably toward the right?
6. Which is the order of increasing acid strength of the following compounds (least first)?
7. Complete the following reaction scheme with the appropriate equilibrium arrow (indicating the higher concentrations at equilibrium)
8. Which of the following molecules are alkanes?
9. What is the IUPAC name for the following molecules?

10. Which of the following molecules are constitutional isomers?
11. Arrange the following groups in the order of increasing priority (lowest first).
12. How many cis/trans isomers are possible for 2,4,6-octatriene?
13. Which of the following alkenes show E/Z isomerism?
I) 1-chloropropene
II) 2,6-dimethyl-2,5-octadiene
III) 3-methylcyclohexene
IV) 3-ethyl-3-methyl-1-pentene
14. What is the structure of (3E, 6Z)-2,9-dimethyl-3,6-decadiene?
15. Which compound does not give two isomers when reacted with Cl₂ / CCl₄?
16. Which of the following pairs represent: (1) enantiomers, (2) diastereomers, (3) constitutional isomers, (4) identical substances?
Which are (5) optically active, (6) optically inactive?
Write the appropriate number next to the letter for each substance.
17. Assign an R or S configuration to each stereocenter.
18. Taxol is an exciting anticancer agent for the treatment of advanced ovarian and breast cancer.
Taxol is derived from the bark of the yew tree (which kills the tree) and by chemical modification of more readily available natural product from the needles of the yew.
The structure of taxol is shown below.
(1) Place an asterisk beside each chiral carbon in Taxol. (3)
(2) What is the configuration of each chiral center? (3)
(3) Next to each functional group in the drawing above, write the number of the appropriate functional group. (3)

19. Vitamin A or retinol is an essential component for the vision receptors in the eyes.
Its structure is shown below.
Reaction of Vitamin A with H₂ over Pd/C produces a substance whose molecular formula is C₂₀H₃₄O.
This substance appeared impure; for example it showed a wide melting range and several bands on a chromatographic column.
Explain the nature of this new material and comment on its optical activity. (12 point)
(1) Explain the nature of this new material and comment on its optical activity. (3)
(2) Explain this chemical reaction in detail. (3)
(3) Place an asterisk beside each chiral carbon in the new materials. (3)
(4) What is the configuration of each chiral center? (3)
20. Complete the following reaction by providing the starting material and reagent and solvent. (3 point)