110年 - 110 國立臺北科技大學_碩士班招生考試_化學工程與生物科技系化學工程碩士班(乙組)：有機化學#102082

選擇題 (25)

1. What hybridization do you expect the carbon atom of the following methyl carbocation to have?
(A)sp (B)sp² (C)sp³(D) The carbon atom is not hybridized.

2. What atom would have a formal charge in the right structure?
(A)A (B)B (C)C(D)D

3. Which of the following describes the relationship between the following two structures?
(A) identical structures(B) resonance forms(C) constitutional isomers (D) different compounds with different compositions

4. Which of the following functional group classifications do not contain oxygen? (A)ether (B)thiol (C)aldehyde (D)amide (E)ester

5. How many constitutional isomers are there with the molecular formula ? (A)3 (B)4 (C)5 (D)6(E)8

6. Which of the following compounds can adopt a chair conformation in which there are no axial methyl groups? (A) 1,1-dimethylcyclohexane (B) cis-1,2-dimethylcyclohexane (C) trans-1,2-dimethylcyclohexane (D) trans-1,3-dimethylcyclohexane

7. Which of the following is the definition of a pair of enantiomers? (A) A pair of structures that are superimposable mirror images of one another (B) A pair of stereoisomers that are non-superimposable mirror images of one another (C) A pair of stercoisomers that are not mirror images of one another (D) A pair of stereoisomers that have equal specific rotations

8. Which of the following compounds is (are) achiral?
(A) only I(B) only II (C) only I and II (D) only II and III (E) I, II, and III

9. What is the relationship between the following pair of structures?
(A) They are enantiomers. (B) They are diastereomers. (C) They are constitutional isomers. (D) They are identical with different conformations.

10. Alkene chemistry is dominated by what type of reaction? (A) substitution (B) electrophilic addition(C) nucleophilic addition (D) elimination

11. Which of the following alkenes exhibit E-Z isomerism?
I. 1-chloropropene II. 2-chloropropene III. 3-chloropropene (A) only I (B) I and II(C) I and II(D) I and IIl

12. Which of the following ions are aromatic species?
(A) I and III (B) II and III (C) II and IV (D) III and IV

13. Rank the following compounds in order of decreasing reactivity to aromatic electrophilic bromination.I. benzene II. toluene III. benzoic acid IV. phenol (A) IV＞II＞I＞III(B) IV＞II＞II＞I(C) II＞I＞IV＞III(D) II ＞II＞IV＞I

14. Where would the compound shown below undergo bromination with Br₂/FeBr₃?
(A) ortho/para position on ring 1 (B) meta position on ring 1 (C) ortho/para position on ring 2 (D) meta position on ring 2

15. In the Friedel-Crafts alkylation of benzene, dialkylation is often a significant by-product. In the Friedel-Crafts acylation of benzene, diacylation is not a significant by-product. Which of the following is the primary reason for this difference? (A) Alkyl groups activate the ring to further substitution, acyl groups deactivate it. (B) AlkyI groups are less sterically hindered than acyl groups. (C) Acyl cations are more difficult to make with Lewis acids. (D) Unlike acyl cations, carbocations can undergo rearrangements.

16. What is the IUPAC name of the following compound?
(A) 3-bromo-2-methylcyclohexene (B) 1-bromo-2-methy1-2-cyclohexene (C) 6-bromo-1-methylcyclohexene (D) 2-bromo-1-methylcyclohexene

17. In the reaction, the "2" stands for (A) two reactants in the reaction. (B) two steps in the reaction. (C) two intermediates in the reaction. (D) bimolecular kinetics for the reaction.

18. Which of the following reacts the fastest by the mechanism? (A) CH₃Br (B) CH₃CH₂Br (C) (CH₃)₂CHBr (D) (CH₃)₃CBr

19. Identify the mechanistic pathways, respectively, for the products in the following reaction.
(A) (B) (C) (D)

20. Which one of the following compounds cannot undergo an E2 reaction? (A) 1-bromo-2,3-dimethylbutane(B) 2-bromo-2,3-dimethylbutane (C) 1-bromo-3,3-dimethyIbutane (D) 1-bromo-2,2-dimethylbutane

21. Which of the following sets of conditions most favors the El mechanism? (A) when the alkyl halide is tertiary and the base is a weak base (B) when the alkyl halide is tertiary and the base is a strong base (C) when the alkyl halide is primary or secondary and the base is a weak base (D) when the alkyl halide is primary or secondary and the base is a strong base

22. Which of the following cannot be made by the reduction of a ketone or aldehyde with NaBH4 in methanol? (A) 1-butanol (B) 2-butanol (C) 2-methyl-1-propanol(D) 2-methyl-2-propanol

23. As a reducing agent, NaBH4 donates a to a _____ to a ketone or aldehyde. (A) proton (B) hydrogen atom (C) hydride ion (D) hydrogen molecule

24. What is the product of the following reaction?
(A) (B) (C)(D)

25. What is the product of the following reaction?
(A) (S)-1,2-propanediol (B) (R)-1,2-propanediol (C) racemic mixture of 1,2-propanediol(D) 1,3-propanediol

申論題 (16)

(a)

(b)

(c)

(d)

(e)

2. Addition of HC1 to 1-isopropylcyclohexene yields a rearranged product. Propose a mechanism, showing the structures of the intermediates and using curved arrows to indicate electron flow in each step. (5 分)