2026 63rd Patent Attorney Second-Round National Qualification Examination
Recommended Post: 【Organic Chemistry】 Solutions to the Patent Attorney Second-Round Organic Chemistry Examination
Overall Assessment: Questions 1 and 2 were easy, so both should have been answered correctly.
Question 1.
Major products A, B, C, D, and E were obtained through the following series of reactions. Answer the following questions. (Assume that appropriate work-up, separation, and purification procedures were performed under suitable conditions at each reaction step.)
⑴ Complete Solution
⑵ Question 1-1. Draw the structure of A and explain the reaction mechanism by which A is obtained from the starting material.
⑶ Answer 1-1. Halogen Addition to an Alkene
⑷ Question 1-2. Draw the structure of B and explain the reaction mechanism by which B is obtained from A.
⑸ Answer 1-2. E2 Elimination Reaction
⑹ Question 1-3. Draw the structures of C, D, and E. Indicate the stereochemistry of the products, if any.
⑺ Answer 1-3. SN2 Reaction, syn Hydrogenation of an Alkyne, Alkene Epoxidation
⑻ Question 1-4. State the name associated with the catalyst used to convert C into D.
⑼ Answer 1-4. Lindlar Catalyst(P-2 catalyst). Involved in the syn hydrogenation of alkynes.
Question 2.
Compound (1R,2S,3S)-2-chloro-1-isopropyl-3-methylcyclohexane (A) was treated with potassium tert-butoxide to obtain major product B. Answer the following questions.
⑴ Complete Solution
⑵ Question 2-1. Draw the stereochemical structure of the compound corresponding to starting material A.
⑶ Answer 2-1. Determining R/S Configurations Using the Vector Cross Product. The most sterically hindered i-Pr group must be oriented horizontally.
⑷ Question 2-2. Draw the stereochemical structure of major product B.
⑸ Question 2-3. Explain the mechanism of the above reaction using chair-conformation molecular structures.
⑹ Answer 2-3. E2 elimination reaction (anti-periplanar
In the above reaction, X and Ha are eliminated.
Question 3.
The following shows part of the mechanism of the ethylene coordination polymerization reaction using a Cp2ZrCl2 catalyst, presented step by step. C is synthesized through catalyst chain extension. Answer the following questions. (Assume that appropriate work-up, separation, and purification procedures were performed under suitable conditions at each reaction step.)
⑴ If you first recall the free-radical polymerization of ethylene, you can understand how chain extension occurs.
⑵ Question 3-1. Draw the structure of A.
⑶ Answer 3-1. The structure on the right below.
⑷ Question 3-2. Draw the structure of B.
⑸ Answer 3-2. The structure in the center below.
⑹ Question 3-3. Draw the structure of C.
⑺ Answer 3-3. C2n-1-alkane and an empty orbital on Zr → Ethylene forms a coordinate bond with the empty d orbital of Zr → C2n+1-alkane and an empty orbital on Zr
⑻ Question 3-4. Explain the two steps through which A and B are formed by coordination polymerization, comparing them with free-radical polymerization.
⑼ Answer 3-4. The radical polymerization of ethylene proceeds as follows. In radical polymerization, a radical containing an unpaired electron moves, a radical initiator is required (a considerable amount of energy is needed because the alkene π bond must be broken), and the reaction can be readily terminated when radicals combine. In contrast, in ethylene coordination polymerization, an electron pair moves, the process is a rearrangement reaction, and the reaction is not readily terminated as long as the catalyst and reactant are present.
Question 4.
Answer the following questions. (Assume that appropriate work-up, separation, and purification procedures were performed under suitable conditions at each reaction step.)
⑴ Question 4-1. Draw the structure of product A.
⑵ Answer 4-1. Overall Wilkinson catalyst reaction : It can be understood as a hydrogenation reaction.
① Since 1 equivalent of hydrogen is provided, the less sterically hindered alkene will react.
② Although the Wilkinson catalyst can also react with ketones, according to the general characteristics of hydrogenation reactions, the more reactive alkene reacts first.
③ The final product A is as follows.
⑶ Question 4-2. Draw the structure of product B, indicating its stereochemistry.
⑷ Answer 4-2.
⑸ Question 4-3. Propose two methods for synthesizing 1-methylcyclohexene from 1-bromocyclohexene and CH3I using an organocopper compound (organocuprate).
⑹ Answer 4-3. Organometallic Reagents
Entered: 2026.08.03 01:12