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1. NaOMe, MeOH, heat ? 2. TMEDA, sec-BuLi, THF; Cul, BrCH₂CH₂CH3 3. NaNH2, NH3 OMe NH₂ OMe OMe OMe Me Me H2N. Me စည်ပင်ခြား MeO N N NH₂ N B C D E

1. NaOMe, MeOH, heat ? 2. TMEDA, sec-BuLi, THF; Cul, BrCH₂CH₂CH3 3. NaNH2, NH3 OMe NH₂ OMe OMe OMe Me Me H2N. Me စည်ပင်ခြား MeO N N NH₂ N B C D E

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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What would be the product of the following sequence:
### Educational Content: Organic Chemistry Reaction Pathways #### Problem Statement Given the starting material and series of reactions below, identify the final organic product in the sequence. #### Starting Material: - **4-Chloropyridine (Cl attached to a pyridine ring)** #### Reaction Sequence: 1. **Sodium methoxide (NaOMe), Methanol (MeOH), Heat** 2. **Tetramethylethylenediamine (TMEDA), sec-Butyllithium (sec-BuLi), Tetrahydrofuran (THF); Copper(I) iodide (CuI), 1-Bromo-3-butane (BrCH₂CH₂CH₂CH₃)** 3. **Sodium amide (NaNH₂), Ammonia (NH₃)** #### Potential Products: - **A**: 4-Methoxypyridine - **B**: 4-(3-Methylbutylamino)-3-methoxypyridine - **C**: 4-(3-Methylamino)-3-methoxypyridine - **D**: 4-(3-Amino)-3-methoxypyridine - **E**: 4-(3-Methyl)-3-methoxypyridine ### Explanation of Reactions: 1. **Substitution Reaction with NaOMe**: - Sodium methoxide in methanol introduces a methoxy group (OMe) to the pyridine ring, replacing the chlorine atom. The intermediate formed here is likely 4-methoxypyridine. 2. **Lithiation and Addition Reaction with TMEDA, sec-BuLi, CuI/BrCH₂CH₂CH₂CH₃**: - In the presence of TMEDA and sec-Butyllithium, lithiation of the intermediate takes place, followed by a copper-catalyzed coupling with 1-Bromo-3-butane, introducing a 3-methylbutyl group to the ring. 3. **Amidation Reaction with NaNH₂ and NH₃**: - Sodium amide in ammonia facilitates an amination reaction, introducing an amino group to the carbon adjacent to the methoxy group. ### Identification of the Final Product: Considering all the substituent additions and rearrangements, follow the mechanism steps carefully to identify which of the products (A through E) matches the transformations
Transcribed Image Text:### Educational Content: Organic Chemistry Reaction Pathways #### Problem Statement Given the starting material and series of reactions below, identify the final organic product in the sequence. #### Starting Material: - **4-Chloropyridine (Cl attached to a pyridine ring)** #### Reaction Sequence: 1. **Sodium methoxide (NaOMe), Methanol (MeOH), Heat** 2. **Tetramethylethylenediamine (TMEDA), sec-Butyllithium (sec-BuLi), Tetrahydrofuran (THF); Copper(I) iodide (CuI), 1-Bromo-3-butane (BrCH₂CH₂CH₂CH₃)** 3. **Sodium amide (NaNH₂), Ammonia (NH₃)** #### Potential Products: - **A**: 4-Methoxypyridine - **B**: 4-(3-Methylbutylamino)-3-methoxypyridine - **C**: 4-(3-Methylamino)-3-methoxypyridine - **D**: 4-(3-Amino)-3-methoxypyridine - **E**: 4-(3-Methyl)-3-methoxypyridine ### Explanation of Reactions: 1. **Substitution Reaction with NaOMe**: - Sodium methoxide in methanol introduces a methoxy group (OMe) to the pyridine ring, replacing the chlorine atom. The intermediate formed here is likely 4-methoxypyridine. 2. **Lithiation and Addition Reaction with TMEDA, sec-BuLi, CuI/BrCH₂CH₂CH₂CH₃**: - In the presence of TMEDA and sec-Butyllithium, lithiation of the intermediate takes place, followed by a copper-catalyzed coupling with 1-Bromo-3-butane, introducing a 3-methylbutyl group to the ring. 3. **Amidation Reaction with NaNH₂ and NH₃**: - Sodium amide in ammonia facilitates an amination reaction, introducing an amino group to the carbon adjacent to the methoxy group. ### Identification of the Final Product: Considering all the substituent additions and rearrangements, follow the mechanism steps carefully to identify which of the products (A through E) matches the transformations
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