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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

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

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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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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