Nifedipine (Procardia and Adalat) belongs to a class of drugs called calcium channelblockers and is effective in the treatment of various types of angina, including that in-duced by exercise. Show how nifedipine can be synthesized from 2-nitrobenzaldehyde,methyl acetoacetate, and ammonia. (Hint: Review the chemistry of your answers toProblems 19.43 and 19.54 and then combine that chemistry to solve this problem.)NOCOOMEMEOOC,acid+ 2`NO2OMe +NH3СНОHNifedipine

2-nitrobenzaldehyde undergoes aldol condensation reaction with methyl acetoacetate followed by…

Answered: Nifedipine (Procardia and Adalat)…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.55P

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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. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.
When bromomethane undergoes solvolysis in a solvent mixture composed of 90% water/10% acetone, the reaction rate is faster than when the same compound is solvolyzed in 80% water/20% acetone. Explain.
The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.
List at least three (3) physical or spectroscopic methods that can be used to differentiate between benzophenone and benzhydrol. Explain how you would differentiate them. What are the most likely impurities to be found in the product of benzhydrol synthesis? How will they affect performance? How can its presence in the final product be reduced?
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.
(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.
Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?
Show how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.
Predict the products obtained from the reaction of triolein with the following reagents.(a) NaOH in water
Predict the products formed when cyclohexanone reacts with the following reagents. (k) sodium cyanide (l) acidic hydrolysis of the product from (k)
Phenylacetone can form two different enols.(a) Show the structures of these enols.(b) Predict which enol will be present in the larger concentration at equilibrium.(c) Propose mechanisms for the formation of the two enols in acid and in base
The formate and methoxide ions are both formed by removing a hydrogen atom from a corresponding neutral compound. Given that each process involves the breaking of an O-H bond, explain why the formate ion is so much more stable than the methoxide ion.

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