讲解一下这道题---能力提升练
1. (2024 全国甲卷, 选考第 36 题, 15 分) 白藜芦醇(化合物 I)具有抗肿瘤、抗氧化、消炎等功效。
以下是某课题组合成化合物 I 的路线。
Chart/Diagram Description:
The image displays a chemical synthesis route starting from compound A and leading to compound I.
- Compound A is a benzene ring with methyl, nitro, and nitro groups substituted. It is labeled A.
- A reacts with Fe/H+ to form B (molecular formula C7H10N2).
- B reacts with 1) NaNO2/HCl and 2) H2O/Δ to form C.
- Compound C is a benzene ring with methyl and two hydroxyl groups substituted. It is labeled C.
- C reacts with (CH3O)2SO2 and NaOH to form D (molecular formula C9H12O2).
- D reacts with NBS to form E (molecular formula C9H11BrO2).
- E reacts with P(OC2H5)3 to form F.
- Compound F is a benzene ring with two methoxy groups substituted, attached to a CH2-P(=O)(OC2H5)2 group. It is labeled F.
- G (molecular formula C8H8O2) and F react with NaH/THF to form H.
- Compound H is a stilbene derivative with methoxy groups on both benzene rings. It is labeled H. The structure shows one benzene ring with two para-methoxy groups and the other benzene ring with one para-methoxy group, connected by a -CH=CH- double bond. However, the structure shown for H appears to have two methoxy groups on one ring (meta or para to each other) and one methoxy group on the other ring, connected by a double bond. Let's assume the diagram is correct as shown. One ring has two H3CO- groups, the other has one H3CO- group.
- H reacts with BBr3 to form I.
- Compound I is a stilbene derivative with hydroxyl groups on both benzene rings, corresponding to the methoxy groups in H. It is labeled I. The structure shows one benzene ring with two HO- groups and the other benzene ring with one HO- group, connected by a -CH=CH- double bond. This is consistent with the de-methylation of H by BBr3.
- Compound G is shown as a benzene ring with two methoxy groups. The formula C8H8O2 suggests a different structure, likely a derivative of benzaldehyde or phenylacetic acid for it to react in a Wittig-like reaction with F. Given the formula and the reaction to form H, G is likely a molecule with a carbonyl group adjacent to the benzene ring with the single methoxy group, e.g., 4-methoxybenzaldehyde. However, the structure shown next to G with formula C8H8O2 is a benzene ring with two methoxy groups (para positions). This seems inconsistent with the formula C8H8O2 and the expected structure for G to form H. Let's describe what's shown. The structure shown next to G is a benzene ring with two OCH3 groups in the para position.
- The reaction from G+F to H is a Wittig-like reaction, where F is a phosphonate. This suggests G should contain a carbonyl group.
Answer the following questions:
(1) A 中的官能团名称为\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_。
(2) B 的结构简式为\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_。
(3) 由 C 生成 D 的反应类型为\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_。
(4) 由 E 生成 F 的化学方程式为\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_。
(5) 已知 G 可以发生银镜反应, G 的化学名称为\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_。
(6) 选用一种鉴别 H 和 I 的试剂并描述实验现象\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_。
(7) I 的同分异构体中, 同时满足下列条件的共有\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_\_种(不考虑立体异构)。
① 含有手性碳(连有 4 个不同的原子或基团的碳为手性碳);
② 含有两个苯环;
③ 含有两个酚羟基;
④ 可发生银镜反应。