Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Pick the reagent(s) and starting material that will produce this compound
### Synthesis Challenge

**Objective:**
Specify a synthetic scheme to produce the compound shown above in the fewest steps possible. Use one of the starting materials provided, along with any of the available reagents. Indicate your answer in the format: starting material number followed by the letters of the reagents used (e.g., 3be).

**Compound to be Synthesized:**
The target compound is a hexenone. The structure includes a cyclohexenone ring connected to a propene chain.

---

**Starting Materials:**

1. \( \text{C}_2\text{H}_5\text{OCCH}_2\text{COC}_2\text{H}_5 \)
2. \( \text{C}_2\text{H}_5\text{OCCH}_2\text{CH}_2 \)
3. Cyclohexanone ethyl ester

---

**Available Reagents:**

- a. \( \text{CH}_3\text{I} \)
- b. \( \text{CH}_3\text{CH}_2\text{I} \)
- c. Propyl iodide
- d. Butyl iodide
- e. Cyclohexyl bromide
- f. \( \text{Br}_2 \)
- g. Allyl bromide
- h. \( \text{Br}_2, \text{hv} \)
- i. Sodium ethoxide (NaOC\(_2\)H\(_5\))
- j. Acidic or Basic hydrolysis: \( \text{H}_3\text{O}^+, \text{heat} \) or \( \text{NaOH, H}_2\text{O}; \text{then} \text{H}_3\text{O}^+, \text{heat} \)

**Instructions:**
Select the most appropriate starting material and reagents to propose a concise synthetic route to obtain the target compound. Input your answer following the example format. 

**Example Response Format:**
3be

Make sure to maximize efficiency and minimize the number of steps in the synthetic process.
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Transcribed Image Text:### Synthesis Challenge **Objective:** Specify a synthetic scheme to produce the compound shown above in the fewest steps possible. Use one of the starting materials provided, along with any of the available reagents. Indicate your answer in the format: starting material number followed by the letters of the reagents used (e.g., 3be). **Compound to be Synthesized:** The target compound is a hexenone. The structure includes a cyclohexenone ring connected to a propene chain. --- **Starting Materials:** 1. \( \text{C}_2\text{H}_5\text{OCCH}_2\text{COC}_2\text{H}_5 \) 2. \( \text{C}_2\text{H}_5\text{OCCH}_2\text{CH}_2 \) 3. Cyclohexanone ethyl ester --- **Available Reagents:** - a. \( \text{CH}_3\text{I} \) - b. \( \text{CH}_3\text{CH}_2\text{I} \) - c. Propyl iodide - d. Butyl iodide - e. Cyclohexyl bromide - f. \( \text{Br}_2 \) - g. Allyl bromide - h. \( \text{Br}_2, \text{hv} \) - i. Sodium ethoxide (NaOC\(_2\)H\(_5\)) - j. Acidic or Basic hydrolysis: \( \text{H}_3\text{O}^+, \text{heat} \) or \( \text{NaOH, H}_2\text{O}; \text{then} \text{H}_3\text{O}^+, \text{heat} \) **Instructions:** Select the most appropriate starting material and reagents to propose a concise synthetic route to obtain the target compound. Input your answer following the example format. **Example Response Format:** 3be Make sure to maximize efficiency and minimize the number of steps in the synthetic process.
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