110年 - 110 國立臺北科技大學_碩士班招生考試_分子科學與工程系有機高分子碩士班(甲組)：有機化學#110883

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)(B)(C)(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 C6H14? (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 miror images of one another (B) A pair of stereoisomers that are non-superimposable mirtor images of one another (C) A pair of stereoisomers 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 IIl (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) clectrophilic 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 IIl (D)I and III

12. Which of the following ions are aromatic species?

(A) I and III (B) II and IIl (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＞II(B) IV＞I＞I＞I(C)!＞I＞IV＞II(D)I＞III＞IV＞I

14. Where would the compound shown below undergo bromination with Br₂/FeBr₃?
(A) ortho/para position on ring I (B) meta position on ring l (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 Fricdel-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, acyI groups deactivate it. (B) Alkyl 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-methyl-2-cyclohexene (C) 6-bromo-1-methylcyclohexene (D) 2-bromo-I-methylcyclohexene

17. In the S_N2 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 theS_N2 mechanism? (A) CH₃Br (B) CH₃；CH₂Br (C) (CH₃)₂CHBr (D) (CH₃)₃CBr

19. Identify the mechanistic pathways, respectively, for the products in the following reaction. (A) E1,S_N1 (B) E1,S_N2 (C) E2,S_N1 (D) E2, S_N2

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-dimethylbutane (D) 1-bromo-2,2-dimethylbutane

21. Which of the following sets of conditions most favors the E1 mechanism? (A) when the alkyI 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 basc

22. Which of the following cannot be made by the reduction of a ketone or aldehyde with NaBH, 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 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 l-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)