Concept explainers
Practice Problem G.1
When farnesol is treated with sulfuric acid, it is converted to bisabolene. Outline a possible mechanism for this reaction.
Interpretation:
The mechanism for the formation of Bisabolene from Farnesol in presence of is to be outlined.
Concept introduction:
Farnesol is a compound that is formed from isoprene compounds. In general, when geranyl pyrophosphate reacts with isopenenyl pyrophosphate, farnesyl pyrophosphate (intermediate for the synthesis of sesquiterpenes) is formed. This, on oxidation can give farnesol.
Concentrated sulfuric acid acts as a strong dehydrating agent and removes the water molecule from alcohols to form unsaturated hydrocarbon.
Answer to Problem 1PP
Solution:
The mechanism for the synthesis of Bisabolene is explained as follows:
Explanation of Solution
During the first step, Farnesol (unsaturated alcohol) reacts with acid (HA = ) to form a hydrated product. Then, the hydrated product formed loses one water molecule to form a carbocation. Consequently, this carbocation rearranges to form a more stable carbocation. At last, the base ( ) abstracts the hydrogen ion from the molecule, forming Bisabolene.
The whole mechanism can be depicted as:
Hence, Bisabolene has been formed from Farnesol in the presence of concentrated sulfuric acid.
The Bisabolene has been synthesized from Farnesol in the presence of concentrated sulfuric acid. The mechanism for the synthesis of Bisabolene is outlined as:
Want to see more full solutions like this?
Chapter G Solutions
Organic Chemistry
Additional Science Textbook Solutions
Essential Organic Chemistry (3rd Edition)
CHEMISTRY-TEXT
Chemistry: Structure and Properties (2nd Edition)
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
General, Organic, and Biological Chemistry: Structures of Life (5th Edition)
Chemistry: A Molecular Approach
- Problum 13.22 Linalool and lavandulol are two of the major compo- nents of lavender oil. (a) What organolithium reagent and carbonyl compound can be used to make each alcohol? (b) How might lavandu- lol be formed by reduction of a carbonyl compound? (c) Why can't linalool be prepared by a similar pathway? OH linalool (three methods) Page 622 OH yo lavandulolarrow_forwardGive detailed Solution with explanation ..give correct answer pleasearrow_forwardGive structural formulas for the reagents, intermediates, and products symbolized by letters in the following equations.arrow_forward
- Nonearrow_forwardIdentify the compounds below that cannot be made via a direct Friedel-Crafts alkylation but can be made via acylation followed by a Clemmensen reduction (to avoid carbocation rearrangements). Select all that apply. A) on B) D) O A В C D C C C Carrow_forwardGive detailed mechanism with explanation needed pleasearrow_forward
- Ch. 15 - Q1 Please help with Organic Chemistry problem Thank youarrow_forwardSuggest a retrosynthesis of product A shown below leading to the starting material B and provide the synthesis of the desired product You may use any other reagents you deem necessary and detailed mechanism is requiredarrow_forwardGive detailed mechanism Solution with explanation needed..don't give Handwritten answerarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningMacroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole