115年 - [無官方正解]115 台灣聯合大學系統_碩士班招生考試_化學類：有機化學#140181

科目：研究所、轉學考(插大)-有機化學 | 年份：115年 | 選擇題數：30 | 申論題數：6

試卷資訊

所屬科目：研究所、轉學考(插大)-有機化學

選擇題 (30)

1. I and II are ______.

(A) constitutional isomers. (B) enantiomers. (C) identical. (D) diastereomers. (E) not isomeric.

2. How many of the following compounds are chiral?

(A) 1 (B) 2 (C) 3 (D) 4 (E) 5

3. What is the major product of the following reaction sequence? (A) I (B) II (C) III (D) IV (E) V

4. An optically active compound, A, with the molecular formula $\mathrm{C_7H_{12}}$ reacts with cold dilute $\mathrm{KMnO_4}$ and gives IR absorption at about $3300~\mathrm{cm^{-1}}$. On catalytic hydrogenation, A is converted to B ($\mathrm{C_7H_{16}}$), and B is also optically active. Which is a possible structure for A?

(A) I (B) II (C) III (D) IV (E) V (F) V

5. What is the major product of the Friedel-Crafts alkylation of benzene with 1-butene and $\mathrm{AlCl}_3$? (A) $n$-butylbenzene (B) 2-phenylbutane (C) 2-methyl-1-phenylpropane (D) $t$-butylbenzene (E) 2,2-diphenylbutane

6. Which of the following factors is favorable for nucleophilicity but not basicity? (A) highly polarizable (B) low electronegativity (C) positively charged (D) sterically hindered (E) negatively charged

7. If a certain hydrocarbon molecule has 10 carbons atoms, one ring and two triple bonds, how many hydrogens does it have? (A) 10 (B) 12 (C) 14 (D) 16 (E) 18

8. How many distinct alkene products are possible, including stereoisomers, when the alkyl bromide below reacts with sodium tert-butoxide?

(A) 1 (B) 2 (C) 3 (D) 4 (E) 5

9. While the carbonyl IR stretching frequency for simple aldehydes, ketones, and carboxylic acids is about $1710~\mathrm{cm}^{-1}$, the carbonyl stretching frequency for amides is about ______. (A) $1700~\mathrm{cm}^{-1}$ (B) $1735~\mathrm{cm}^{-1}$ (C) $1800~\mathrm{cm}^{-1}$ (D) $1660~\mathrm{cm}^{-1}$ (E) $2200~\mathrm{cm}^{-1}$

10. What reagent is used to convert pentanamide to 1-pentanamine? (A) $\mathrm{POCl}_3$ (B) CuCN (C) $\mathrm{CH}_3\mathrm{MgBr}$ (D) $\mathrm{SOCl}_2$ (E) LiAlH₄

11. Predict the order of pKa of the following carboxylic acid.

(A) $\mathrm{I} > \mathrm{II} > \mathrm{III}$ (B) $\mathrm{III} > \mathrm{II} > \mathrm{I}$ (C) $\mathrm{II} > \mathrm{I} > \mathrm{III}$ (D) $\mathrm{III} > \mathrm{I} > \mathrm{II}$ (E) $\mathrm{II} > \mathrm{III} > \mathrm{I}$

12. Which of these could be resolved into separate enantiomers? (A) 4-Methyl-1-pentanamine (B) 4-Methyl-2-pentanamine (C) $N$-Methyl-1-butanamine (D) $N,N$-Dimethyl-1-propanamine (E) $N$-Butyltrimethylammonium bromide

13. When 3-methyl-2-pentene is treated with mercuric acetate, $\mathrm{Hg(O_2CCH_3)_2}$, in a THF-$t$-butyl alcohol mixture and the resulting product is reacted with $\mathrm{NaBH_4}$ in basic solution, the principal product formed is which of these? (A) 3-methyl-3-pentanol (B) 3-$t$-butoxy-3-methylpentane (C) 3-methyl-2-pentanol (D) 2-$t$-butoxy-3-methylpentane (E) 1-$t$-butoxy-3-methylpentane

14. How many of the following compounds are aromatic? (A) 4 (B) 5 (C) 6 (D) 7 (E) 8

15. How many of the following reactions give the correct major product?

(A) 1 (B) 2 (C) 3 (D) 4 (E) 5

16. What is the major product of the reaction shown below?

17. Predict the major product for the following reaction?

18. Rank of the acidity of the following compounds from high to low? (A) ii > iii > iv > i > v (B) iii > i > iv > v > ii (C) iv > i > iii > v > ii (D) v > iv > i > iii > ii (E) i > iv > v > ii > iii