Interpretation:
A synthesis of nifedipine from 2-nitrobenzaldehyde, methyl acetoacetate and ammonia has to be given.
Concept introduction:
Aldol condensation:
Aldol reaction is an addition reaction of
Michael reaction:
The reaction occurs with a variety of
The donor compound of this reaction includes
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Chapter 19 Solutions
Organic Chemistry
- 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_forwardTreatment of pentanedioic (glutaric) anhydride with ammonia at elevated temperature leads to a compound of molecular formula C5H7NO2. What is the structure of this product? [Hint: You need to think about the reactivity not only of acid anhydrides but also of amides and carboxylic acids]arrow_forwardWhy do you wash the dichloromethane solution of your reductive amination product with sodium bicarbonate, rather than dilute aqueous HCl? a) Sodium bicarbonate is a good method of removing aldehydes from organic solvent.b) The amine product will be protonated by acid and remain in the aqueous layer as a salt.c) Sodium bicarbonate transfers the amine starting material into the aqueous layer.d) Sodium bicarbonate reacts with leftover NaBH(OAc)3 and removes it from the mixture.arrow_forward
- A step in a synthesis of PGE1 (prostanglandin E1, alprostadil) is reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Alprostadil is used as temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation. Propose a mechanism for formation of This bromolactone, and account for the observed stereochemistry of each substituent on the cyclohexane ring.arrow_forwardCancer of the prostate is the second leading cause of cancer deaths among American males, exceeded only by lung cancer. One treatment of prostate cancer is based on the fact that testosterone and androsterone (both androgens) enhance the proliferation of prostate tumors. The drug flutamide (an antiandrogen) reduces the level of androgens in target tissues and is currently used to prevent and treat prostate cancer.Propose a synthesis of flutamide from trifluoromethylbenzenearrow_forwardShow reagents and experimental conditions by which oxanamide can be synthesized from butanal.arrow_forward
- Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. Draw a diagram to show the mechanism of the reaction of either propanal or propanone with acidified potassium cyanide.arrow_forwardthe organic compound 2-heptanone, belonging to the ketone family, is responsible for the strong penetrating odor in Roquefort cheeses. Starting from acetylene as the starting reagent, propose a synthesis line with the reaction mechanisms involved for the synthetic obtaining of 2-heptanone and use it as a food additive in analogous cheeses.arrow_forwardWhich of the two aromatic rings of phenyl benzoate would undergo nitration? What is the structure of the product?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning