Concept explainers
Interpretation: A mechanism has to be proposed for the given rearrangement reaction.
Concept introduction:
Benzil-benzilic acid rearrangement reaction:
Benzil-benzilic acid rearrangement reaction is a base catalysed reaction in which,
1,2-diketones are allowed to react with base followed by the acidification to form
Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.
Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.
Curved arrows used to understand a reaction mechanism.
Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of
Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.
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Chapter 17 Solutions
Organic Chemistry
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- Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardPropose a mechanism for the acid-catalyzed reaction of benzaldehyde with methanol to give benzaldehyde dimethyl acetal.arrow_forwardBisphenol A is made on a large scale by a condensation of phenol with acetone. Suggest an appropriate catalyst, and propose a mechanism for this reaction.arrow_forward
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning