详细讲解一下这道化学题,如果有化学反应相关的动画演示更好---The extracted content from the image is as follows:
**Overall Context:**
19. (14分) Aromatic compounds containing a furan skeleton are of important value in the fields of environmental chemistry and materials science. A synthesis route for an aromatic compound containing a furan skeleton is as follows:
**Synthesis Pathway Description:**
The image displays a multi-step chemical synthesis pathway involving several intermediate compounds (A to H, and M to N).
* **Molecule A:** A benzene ring substituted with a hydroxyl (-OH) group and a carboxyl (-COOH) group in an ortho relationship.
* **Reaction A → B:**
* Reagents: CH3OH, concentrated H2SO4, Δ (heat).
* Product B: Chemical formula C8H8O3. Structure: A benzene ring substituted with a hydroxyl (-OH) group and a methyl ester (-COOCH3) group in an ortho relationship.
* **Reaction B → C:**
* Reagent: LiAlH4.
* Product C: Chemical formula C7H8O2. Structure: A benzene ring substituted with a hydroxyl (-OH) group and a hydroxymethyl (-CH2OH) group in an ortho relationship.
* **Reaction C → D:**
* Reagents: O2, Pt3Pd/C.
* Product D: Structure: A benzene ring substituted with a hydroxyl (-OH) group and an aldehyde (-CHO) group in an ortho relationship.
* **Reaction D → E:**
* Reagents: PPh3, CBr4, base.
* Product E: Structure: A benzene ring substituted with a hydroxyl (-OH) group and a dibromomethylene (-CH=CBr2) group in an ortho relationship.
* **Reaction E → F:**
* Reagents: CuI, K3PO4, Δ (heat).
* Product F: Structure: A benzofuran system (a benzene ring fused to a furan ring). The furan ring has a bromine atom at position 2 (adjacent to the oxygen bridgehead) and a phenyl group at position 3.
* **Reaction F → G:**
* Reagents: Phenylboronic acid (PhB(OH)2, denoted as -B(OH)2 in the diagram), "一定条件" (certain conditions).
* Product G: Chemical formula C14H10O. (The structure is not explicitly drawn, but given the formula and the subsequent reaction to H, it's implied to be 3-phenylbenzofuran).
* **Reaction G → H:**
* Reagents: An N-bromosuccinimide derivative (specifically, 3-bromo-1-oxoisoindoline-2-yl, depicted with a nitrogen atom bonded to a bromine atom, within a five-membered ring containing two carbonyl groups and fused to a benzene ring), and "一定条件" (certain conditions).
* Product H: Structure: A benzofuran system. The furan ring has a bromine atom at position 2 and a phenyl group at position 3. Additionally, the benzene ring has another bromine atom at position 7 (para to the furan oxygen's bridgehead).
* **Molecule M:**
* Structure: A benzofuran system. The furan ring has a phenylethynyl group (-C≡C-Ph) attached at position 2.
* **Reaction M → N:**
* Reagents: i) ≡-TMS, "一定条件" (certain conditions); ii) K2CO3. Then PtCl2, Δ (heat).
* Product N: Structure: A benzofuran system. The furan ring has a phenyl group at position 2 and another phenyl group at position 3.
**Questions:**
Answer the following questions:
(1) The chemical equation for A→B is ______.
(2) C→D achieved the transformation from ______ to ______ (fill in functional group names).
(3) The reaction type for G→H is ______.
(4) Among the isomers of E, the number of isomers containing a benzene ring (without other rings) and with the ratio of hydrogen atoms in different chemical environments being 3:2:1 is ______ species.
(5) In the triple bond addition reaction of M→N, if the benzene ring involved in bonding and its reaction position remain unchanged, the structural formula of the byproduct that is an isomer of N is ______.
(6) Referring to the above route, design the following transformation. The structural formulas of X and Y are ______ and ______.
**Sub-diagram for Question (6):**
A three-step synthesis pathway is shown:
* **Step 1:**
* Starting Material: A fused polycyclic system consisting of a central benzene ring flanked by two thiophene rings, forming a benzo[1,2-b:4,5-b']dithiophene core. This core is substituted with two bromine atoms at positions 3 and 6 (on the thiophene rings). (Specifically, 3,6-dibromobenzo[1,2-b:4,5-b']dithiophene).
* Reagents: NaOH, C2H5OH, Δ (heat).
* Product: X (structure to be determined).
* **Step 2 (X → Y):**
* Reagent: An N-bromosuccinimide derivative (3-bromo-1-oxoisoindoline-2-yl, same as in G→H step).
* Product: Y (structure to be determined).
* **Step 3 (Y → Final Product):**
* Reagents: Phenylboronic acid (PhB(OH)2, denoted as -B(OH)2), "一定条件" (certain conditions).
* Final Product: A fused polycyclic system identical to the starting material's core (benzo[1,2-b:4,5-b']dithiophene), but with two phenyl groups (-Ph) replacing the bromine atoms at positions 3 and 6. (Specifically, 3,6-diphenylbenzo[1,2-b:4,5-b']dithiophene).