OH H* catalyst ge raniol (rose oil extract) beta-myrcene

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Chapter1: Chemical Foundations
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Alcohols are great starting molecules for synthesis, as well as intermediates, since they can act by turns as acids, bases, nucleophiles, or electrophiles (with proper derivatization).  While fossil fuel hydrocarbons have provided us with a synthetic starting point via halogenation, Nature has provided us with the starting point of alcohols.  Geraniol is an alcohol that is extractable from various plants, such as roses.  While a fragrance in its own right, it is sometimes used as a feedstock to synthesize beta-myrcene, a versatile synthetic intermediate in the flavor and fragrance industry.  Show a curved-arrow mechanism whereby geraniol might be transformed into beta-myrcene.  It may be helpful to consider this reaction in the presence of an acid catalyst.

 

 

**Geraniol to Beta-Myrcene Conversion**

This image illustrates the chemical conversion of geraniol to beta-myrcene using an acid catalyst (H⁺). 

**Chemical Structures:**

1. **Geraniol (Rose Oil Extract):** 
   - Structure: A linear terpene with an alcohol group (OH) at one end.
   - Notable Features: Contains a double bond in the middle of the carbon chain and an OH group.

2. **Reaction Conditions:**
   - An acid catalyst (H⁺) is used to facilitate the conversion.

3. **Beta-Myrcene:**
   - Structure: A more open-chain terpene with two double bonds.
   - Notable Features: Lacks the alcohol group due to its conversion from geraniol.

**Explanation of the Reaction:**

The acid-catalyzed dehydration of geraniol results in the removal of the hydroxyl group and the formation of additional double bonds, leading to the structure of beta-myrcene. This reaction showcases a common method of modifying terpene structures by eliminating functional groups and rearranging carbon-carbon double bonds.
Transcribed Image Text:**Geraniol to Beta-Myrcene Conversion** This image illustrates the chemical conversion of geraniol to beta-myrcene using an acid catalyst (H⁺). **Chemical Structures:** 1. **Geraniol (Rose Oil Extract):** - Structure: A linear terpene with an alcohol group (OH) at one end. - Notable Features: Contains a double bond in the middle of the carbon chain and an OH group. 2. **Reaction Conditions:** - An acid catalyst (H⁺) is used to facilitate the conversion. 3. **Beta-Myrcene:** - Structure: A more open-chain terpene with two double bonds. - Notable Features: Lacks the alcohol group due to its conversion from geraniol. **Explanation of the Reaction:** The acid-catalyzed dehydration of geraniol results in the removal of the hydroxyl group and the formation of additional double bonds, leading to the structure of beta-myrcene. This reaction showcases a common method of modifying terpene structures by eliminating functional groups and rearranging carbon-carbon double bonds.
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Elimination reaction is a type of reaction is mainly used to transform saturated compounds (organic compounds which contain single carbon-carbon bonds) to unsaturated compounds (compounds which feature double or triple carbon-carbon bonds). Besides, it is an important method for the preparation of alkenes.

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