Each arrow below represents a step. In the correct order, write/draw in the missing reagent(s) or reactants needed above each reaction arrow to complete each two-step syntheses and to obtain the major product shown. H3C-OH НО. DI.. H CH3 D = deuterium

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Chapter1: Chemical Foundations
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**Synthesis Problem for Educational Website**

**Objective:**
Each arrow below represents a reaction step. The task is to determine and write or draw the missing reagents or reactants above each reaction arrow. Each series is a two-step synthetic process intended to yield the major product shown.

---

**Reactions and Products:**

1. **Reaction Sequence:**
   - **Starting Compound:** Methanol (CH₃OH)
   - **Product:** tert-Butyl methyl ether (C₄H₉OCH₃)
   
   **Reaction Arrows:**
   - First arrow: Missing reagents to convert methanol into an intermediate.
   - Second arrow: Missing reagents to complete the synthesis to tert-butyl methyl ether.

2. **Reaction Sequence:**
   - **Starting Compound:** 1,3-Diiodobenzene
   - **Product:** Phenyloxirane
   
   **Reaction Arrows:**
   - First arrow: Missing reagents to convert 1,3-diiodobenzene into an intermediate.
   - Second arrow: Missing reagents to achieve the final product, phenyloxirane.

3. **Reaction Sequence:**
   - **Starting Compound:** 2-Deutero-1-hydroxycyclopentanol (with deuterium, D)
   - **Product:** 1-Deuterocyclopent-2-enol
   
   **Reaction Arrows:**
   - First arrow: Missing reagents necessary for dehydration or structural rearrangement.
   - Second arrow: Missing reagents or conditions to obtain the cyclopentenol with deuterium.

4. **Reaction Sequence:**
   - **Starting Compound:** 2-Methylbutan-2-ol
   - **Product:** (E)-4-Methylpent-3-en-1-ol
   
   **Reaction Arrows:**
   - First arrow: Missing reagents for dehydrogenation or elimination.
   - Second arrow: Missing reagents for further modification to achieve specified product structure.

---

**Target Product Observations:**
- The transformation from starting materials involves substitutions, eliminations, and rearrangements.
- Understanding functional group interconversions and appropriate conditions (acidity, temperature, catalysts) is crucial.
- *Note:* D (Deuterium) is an isotope of hydrogen, typically used to track molecules.

For instructors: Encourage students to think about reaction mechanisms and explore various synthetic routes.
Transcribed Image Text:**Synthesis Problem for Educational Website** **Objective:** Each arrow below represents a reaction step. The task is to determine and write or draw the missing reagents or reactants above each reaction arrow. Each series is a two-step synthetic process intended to yield the major product shown. --- **Reactions and Products:** 1. **Reaction Sequence:** - **Starting Compound:** Methanol (CH₃OH) - **Product:** tert-Butyl methyl ether (C₄H₉OCH₃) **Reaction Arrows:** - First arrow: Missing reagents to convert methanol into an intermediate. - Second arrow: Missing reagents to complete the synthesis to tert-butyl methyl ether. 2. **Reaction Sequence:** - **Starting Compound:** 1,3-Diiodobenzene - **Product:** Phenyloxirane **Reaction Arrows:** - First arrow: Missing reagents to convert 1,3-diiodobenzene into an intermediate. - Second arrow: Missing reagents to achieve the final product, phenyloxirane. 3. **Reaction Sequence:** - **Starting Compound:** 2-Deutero-1-hydroxycyclopentanol (with deuterium, D) - **Product:** 1-Deuterocyclopent-2-enol **Reaction Arrows:** - First arrow: Missing reagents necessary for dehydration or structural rearrangement. - Second arrow: Missing reagents or conditions to obtain the cyclopentenol with deuterium. 4. **Reaction Sequence:** - **Starting Compound:** 2-Methylbutan-2-ol - **Product:** (E)-4-Methylpent-3-en-1-ol **Reaction Arrows:** - First arrow: Missing reagents for dehydrogenation or elimination. - Second arrow: Missing reagents for further modification to achieve specified product structure. --- **Target Product Observations:** - The transformation from starting materials involves substitutions, eliminations, and rearrangements. - Understanding functional group interconversions and appropriate conditions (acidity, temperature, catalysts) is crucial. - *Note:* D (Deuterium) is an isotope of hydrogen, typically used to track molecules. For instructors: Encourage students to think about reaction mechanisms and explore various synthetic routes.
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