Propose an efficient synthesis for the following transformation. The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A В C D t-BUOK HBr, ROOR EtONa HBr E F G H conc. H2SO4, heat H2SO4, H20, HgSO4 1) O3; 2) DMS 1) xs NaNH2; 2) H2O K 1) R2BH; 2) H2O2, NaOH Mel HC=CNa Br2, hv

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Chapter1: Chemical Foundations
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**Propose an Efficient Synthesis for the Following Transformation**

The transformation involved is a conversion of a cyclopentane ring to a linear carbon skeleton with an aldehyde group. The goal is to determine the appropriate reagents from a list provided to carry out this transformation in the correct sequence.

Below are the available reagents, labeled A through L:

- **A:** t-BuOK
- **B:** HBr, ROOR
- **C:** EtONa
- **D:** HBr
- **E:** conc. H₂SO₄, heat
- **F:** H₂SO₄, H₂O, HgSO₄
- **G:** 1) O₃; 2) DMS
- **H:** 1) xs NaNH₂; 2) H₂O
- **I:** 1) R₂BH; 2) H₂O₂, NaOH
- **J:** MeI
- **K:** HC≡CNa
- **L:** Br₂, hv

**Instructions:** 
- Utilize the correct reagents in order.
- Provide the answer as a continuous string of letters (e.g., "EBF").
- If multiple solutions exist, provide only one.

Note: This problem set focuses on understanding and applying the order of chemical reactions to achieve the desired structural transformation.
Transcribed Image Text:**Propose an Efficient Synthesis for the Following Transformation** The transformation involved is a conversion of a cyclopentane ring to a linear carbon skeleton with an aldehyde group. The goal is to determine the appropriate reagents from a list provided to carry out this transformation in the correct sequence. Below are the available reagents, labeled A through L: - **A:** t-BuOK - **B:** HBr, ROOR - **C:** EtONa - **D:** HBr - **E:** conc. H₂SO₄, heat - **F:** H₂SO₄, H₂O, HgSO₄ - **G:** 1) O₃; 2) DMS - **H:** 1) xs NaNH₂; 2) H₂O - **I:** 1) R₂BH; 2) H₂O₂, NaOH - **J:** MeI - **K:** HC≡CNa - **L:** Br₂, hv **Instructions:** - Utilize the correct reagents in order. - Provide the answer as a continuous string of letters (e.g., "EBF"). - If multiple solutions exist, provide only one. Note: This problem set focuses on understanding and applying the order of chemical reactions to achieve the desired structural transformation.
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