The biological conversation of geranyl diphosphate to geraniol occurs via an Sn1 pathway. The product is a fragrant alcohol found in roses and used in perfume. The "OPP" is a disphosphate group and is essentially a very good leaving group. a. Provide a mechanism for this reaction (including curved arrows) b. Why is the carbocation intermediate stable even though primary carbocations are unstable? H20 OPP OH

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2. The biological conversion of geranyl diphosphate to geraniol occurs via an S<sub>N</sub>1 pathway. The product is a fragrant alcohol found in roses and used in perfume. The "OPP" is a diphosphate group and is essentially a very good leaving group.

a. Provide a mechanism for this reaction (including curved arrows).

b. Why is the carbocation intermediate stable even though primary carbocations are unstable?

**Chemical Reaction Illustration:**

- **Reactant:** Geranyl diphosphate is depicted with a long carbon chain, including two double bonds, and an "OPP" group at the end representing the diphosphate group.
  
- **Reagent:** H<sub>2</sub>O (water).

- **Product:** Geraniol is shown with a similar carbon chain, but now terminating with an alcohol group (OH) instead of the diphosphate group.

**Explanation:**

- **Mechanism Suggestion:**
  - The leaving of the diphosphate group ("OPP") from the compound forms a carbocation.
  - Curved arrows indicate the flow of electrons during the formation of the carbocation and later during the addition of water to form the alcohol.

- **Stability of Carbocation:**
  - Despite the usual instability of primary carbocations, this intermediate is stabilized by structural aspects or electronic effects present in the molecule, such as resonance or hyperconjugation.
Transcribed Image Text:2. The biological conversion of geranyl diphosphate to geraniol occurs via an S<sub>N</sub>1 pathway. The product is a fragrant alcohol found in roses and used in perfume. The "OPP" is a diphosphate group and is essentially a very good leaving group. a. Provide a mechanism for this reaction (including curved arrows). b. Why is the carbocation intermediate stable even though primary carbocations are unstable? **Chemical Reaction Illustration:** - **Reactant:** Geranyl diphosphate is depicted with a long carbon chain, including two double bonds, and an "OPP" group at the end representing the diphosphate group. - **Reagent:** H<sub>2</sub>O (water). - **Product:** Geraniol is shown with a similar carbon chain, but now terminating with an alcohol group (OH) instead of the diphosphate group. **Explanation:** - **Mechanism Suggestion:** - The leaving of the diphosphate group ("OPP") from the compound forms a carbocation. - Curved arrows indicate the flow of electrons during the formation of the carbocation and later during the addition of water to form the alcohol. - **Stability of Carbocation:** - Despite the usual instability of primary carbocations, this intermediate is stabilized by structural aspects or electronic effects present in the molecule, such as resonance or hyperconjugation.
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