Interpretation:
The three sequential pericyclic reactions involved in synthesizing coronafacic acid are to be identified. A mechanism for the overall transformation is to be proposed. How the synthesis can be completed is also to be indicated.
Concept introduction:
In electrocyclic reactions cyclic
In cycloaddition reactions two unsaturated molecules add to one another to yield a cyclic product.
In basic solutions the conjugated enones tautomerize and exist as tautomers.
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Chapter 30 Solutions
Organic Chemistry
- Propose a mechanism for the following reaction, an important step in the laboratory synthesis of proteins:arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardAldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forward
- 18) The following reaction undergoes three distinct steps: imine formation, electrophilic aromatic substitution, and decarboxylation. Draw each of the intermediates from each of these three steps as well as the final product. BS NH₂ OH heatarrow_forwardb) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OHarrow_forwardWhat is the synthesis and mechanism for the following?arrow_forward
- Voltooi die volgende reaksie en stel 'h meganisme voor. Complete the following reaction and propose a mechanism. 1) CO2, P, A 2) H20, H*arrow_forwardPredict the intermediates and final product. Provide a rational mechanism.arrow_forwardShow two reaction schemes to synthesize the following compounds. Pick one reactionscheme and draw the step-by-step reaction mechanismarrow_forward
- Propose a mechanism.arrow_forwardBr Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:arrow_forwardgive a reaction mechanism provided the following conditionsarrow_forward