Concept explainers
Interpretation:
The synthesis for the given intermediate from the compound A has to be proposed.
Concept introduction:
Enamine:
An enamine is a compound where the lone pair of electrons in the nitrogen atom of
It is formed by the reaction of a
Stork Enamine reaction:
In the reaction, enamine formation from a ketone or aldehyde occurs. Then the addition of this enamine to an
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Chapter 19 Solutions
OWL V2 with MindTap Reader and Student Solutions Manual eBook for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Synthesize benzylamine from benzaldehydearrow_forwardThe following intermediate was needed for the synthesis of tamoxifen, a widely used antiestrogen drug for treating estrogen-dependent cancers such as breast and ovarian cancer. Needed for the (A) synthesis of tamoxifen Propose a synthesis for this intermediate from compound A.arrow_forwardPropose the synthesis for the following transformations.arrow_forward
- Identify A, B, and C, three intermediates in the synthesis of the pain reliever and anesthetic fentanyl.arrow_forwardDescribe how the following compounds could be prepared from cyclohexanone using an enamine intermediate:arrow_forwardFollowing 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_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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