Propose a synthesis of octane starting from 1-pentyne. Specify the reagents you would use to carry it out. If two or more routes to the same product are possible, show only one of them. (Specify reagents using letters from the table, the first reagent on the left. Example: ab) a.1. BH3 2. CH3COOH Reagents available c. O8O4, H₂O2 The reagents are: d.1. Hg(OAc)2, H₂O 2. NaBH4 g. H₂ / Ni h. 2 mol Na/ 2. CH3 CH₂ CH₂ Br NH3 (/) f. H₂ Lindlar catalyst b. H,O, H2SO4, HgSO e.1. NaNH, / NH3

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
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**Propose a Synthesis of Octane Starting from 1-Pentyne**

In this exercise, we aim to synthesize octane beginning with 1-pentyne. To achieve this, specify the reagents you would use. If two or more routes to the same product are possible, show only one of them.

**Instructions:**

Specify reagents using letters from the table, listing the first reagent on the left. For example, indicate a sequence of reagents as: `ab`.

**Reagents Available:**

- **a.** 
  1. BH₃ 
  2. CH₃COOH

- **b.** 
  1. H₂O, H₂SO₄, HgSO₄

- **c.** 
  1. OsO₄, H₂O₂

- **d.** 
  1. Hg(OAc)₂, H₂O 
  2. NaBH₄

- **e.** 
  1. NaNH₂ / NH₃ 
  2. CH₃CH₂CH₂CH₂Br

- **f.** 
  1. H₂ / Lindlar catalyst

- **g.** 
  1. H₂ / Ni

- **h.** 
  1. 2 mol Na / NH₃ (l) 

**Answer Box for Reagents:** [ ____ ] 

*Fill in your proposed reagent sequence in the box provided.*
Transcribed Image Text:**Propose a Synthesis of Octane Starting from 1-Pentyne** In this exercise, we aim to synthesize octane beginning with 1-pentyne. To achieve this, specify the reagents you would use. If two or more routes to the same product are possible, show only one of them. **Instructions:** Specify reagents using letters from the table, listing the first reagent on the left. For example, indicate a sequence of reagents as: `ab`. **Reagents Available:** - **a.** 1. BH₃ 2. CH₃COOH - **b.** 1. H₂O, H₂SO₄, HgSO₄ - **c.** 1. OsO₄, H₂O₂ - **d.** 1. Hg(OAc)₂, H₂O 2. NaBH₄ - **e.** 1. NaNH₂ / NH₃ 2. CH₃CH₂CH₂CH₂Br - **f.** 1. H₂ / Lindlar catalyst - **g.** 1. H₂ / Ni - **h.** 1. 2 mol Na / NH₃ (l) **Answer Box for Reagents:** [ ____ ] *Fill in your proposed reagent sequence in the box provided.*
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