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Which of the following synthetic sequences would not accomplish the transformation shown? (A) (B) (C) (D) OA OB O C OD TSCI pyridine PBr3 OH SOCI₂ pyridine NaCECH Mgº Et₂0 BrMg, 1) DMSO, (COCI) 2 1) 2) NEt3 H-B NaCECH 1) 2) H₂O₂, NaOH , 요 2) H₂O 1) 2) H₂O tym H 1) TSCI pyridine 2) IBUOK H₂ Lindlar's cat. 1) TSCI pyridine 2) IBUOK 1) BH3-THF 2) H₂O₂, NaOH 1) 03 2) Me₂S 1) H₂, Pt 2) H3O+ PCC Dess-Martin Periodinane CH₂Cl2

Which of the following synthetic sequences would not accomplish the transformation shown? (A) (B) (C) (D) OA OB O C OD TSCI pyridine PBr3 OH SOCI₂ pyridine NaCECH Mgº Et₂0 BrMg, 1) DMSO, (COCI) 2 1) 2) NEt3 H-B NaCECH 1) 2) H₂O₂, NaOH , 요 2) H₂O 1) 2) H₂O tym H 1) TSCI pyridine 2) IBUOK H₂ Lindlar's cat. 1) TSCI pyridine 2) IBUOK 1) BH3-THF 2) H₂O₂, NaOH 1) 03 2) Me₂S 1) H₂, Pt 2) H3O+ PCC Dess-Martin Periodinane CH₂Cl2

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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
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The image presents a question about synthetic sequences in organic chemistry. The task is to identify which of the given sequences would not accomplish the specified transformation. ### Transformation Goal: Convert 1-butanol (an alcohol) into butanal (an aldehyde). #### Synthetic Sequences: - **(A):** 1. Treat with TsCl and pyridine. 2. React with NaC≡CH. 3. Hydroboration-oxidation sequence (H-BR and H2O2, NaOH). - **(B):** 1. Convert with PBr3. 2. Grignard formation with Mg° in Et2O. 3. Reaction with formaldehyde (H2CO), followed by water. 4. Treat with TsCl, pyridine, and tBuOK. 5. Perform hydroboration-oxidation (BH3-THF, H2O2, NaOH). 6. Oxidize using PCC. - **(C):** 1. Swern oxidation with DMSO, (COCl)2, and NEt3. 2. Create a Grignard reagent with BrMg. 3. React with an ether-silicon group. 4. Treat with TsCl, pyridine, and tBuOK. 5. Catalytic hydrogenation (H2, Pt) followed by acidic workup (H3O+). 6. Final oxidation using Dess-Martin Periodinane in CH2Cl2. - **(D):** 1. Chlorinate with SOCl2 and pyridine. 2. React with sodium acetylide. 3. Hydrogenate using Lindlar's catalyst. 4. Perform ozonolysis (O3) and reduction (Me2S). The challenge is to determine which sequence does not successfully produce the aldehyde from the starting alcohol. **Answer Options:** - A - B - C - D These sequences involve typical organic reactions such as chlorination, Grignard formation, and oxidation, each with a series of reagents and catalysts to achieve the transformation.
Transcribed Image Text:The image presents a question about synthetic sequences in organic chemistry. The task is to identify which of the given sequences would not accomplish the specified transformation. ### Transformation Goal: Convert 1-butanol (an alcohol) into butanal (an aldehyde). #### Synthetic Sequences: - **(A):** 1. Treat with TsCl and pyridine. 2. React with NaC≡CH. 3. Hydroboration-oxidation sequence (H-BR and H2O2, NaOH). - **(B):** 1. Convert with PBr3. 2. Grignard formation with Mg° in Et2O. 3. Reaction with formaldehyde (H2CO), followed by water. 4. Treat with TsCl, pyridine, and tBuOK. 5. Perform hydroboration-oxidation (BH3-THF, H2O2, NaOH). 6. Oxidize using PCC. - **(C):** 1. Swern oxidation with DMSO, (COCl)2, and NEt3. 2. Create a Grignard reagent with BrMg. 3. React with an ether-silicon group. 4. Treat with TsCl, pyridine, and tBuOK. 5. Catalytic hydrogenation (H2, Pt) followed by acidic workup (H3O+). 6. Final oxidation using Dess-Martin Periodinane in CH2Cl2. - **(D):** 1. Chlorinate with SOCl2 and pyridine. 2. React with sodium acetylide. 3. Hydrogenate using Lindlar's catalyst. 4. Perform ozonolysis (O3) and reduction (Me2S). The challenge is to determine which sequence does not successfully produce the aldehyde from the starting alcohol. **Answer Options:** - A - B - C - D These sequences involve typical organic reactions such as chlorination, Grignard formation, and oxidation, each with a series of reagents and catalysts to achieve the transformation.
**What is the major product of the following reaction sequence?** The reaction sequence involves: 1) The first step with the reagent 9-BBN. 2) The use of H₂O₂ and NaOH. 3) Followed by the reaction with CrO₃ and H₂O. Below the sequence, four potential products are depicted: - **(A)** A compound with a carbonyl group attached to a cyclohexane ring and a propyl chain. - **(B)** A hexanoic acid with a cyclohexane ring. - **(C)** A hexanol with a cyclohexane ring. - **(D)** A hexanal with a cyclohexane ring. Each product option is labeled (A), (B), (C), and (D). The possible answers are: - ○ A - ○ B - ○ C - ○ D
Transcribed Image Text:**What is the major product of the following reaction sequence?** The reaction sequence involves: 1) The first step with the reagent 9-BBN. 2) The use of H₂O₂ and NaOH. 3) Followed by the reaction with CrO₃ and H₂O. Below the sequence, four potential products are depicted: - **(A)** A compound with a carbonyl group attached to a cyclohexane ring and a propyl chain. - **(B)** A hexanoic acid with a cyclohexane ring. - **(C)** A hexanol with a cyclohexane ring. - **(D)** A hexanal with a cyclohexane ring. Each product option is labeled (A), (B), (C), and (D). The possible answers are: - ○ A - ○ B - ○ C - ○ D
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