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
- In the synthesis of 1-phenylazo-2-naphthol (or Sudan I), phenyldiazonium reacts with β-naphthol. Draw the resonance structures of the intermediate formed when the diazonium ion attacks a) carbon 1 and b) carbon 3 of β-naphthol. Based on the resonance structures, explain why attack on carbon 1 is preferred.arrow_forwardIn preparation of dibenzalacetone from benzaldehyde: Give two techniques that can be used to purify partially air-oxidized benzaldehyde. Indicate how each technique works in purifying benzaldebyde from its air-oxidized impurities.arrow_forward4) Write the reaction between cyclohexanecarboxylic acid and thionyl chloride showing all three products (two gaseous and one liquid). Take the liquid product and treat it with 2 moles of dimethylamine in benzene as the solvent. You get two products. What are they? Draw their formulae and write their names.arrow_forward
- Why is methyl salicylate so easily absorbed through the skin?arrow_forwardThe 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.arrow_forwardWhen 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.arrow_forward
- Which of the following sets of reagents would not be an acceptable method for the preparation of ethylacetate? acetic acid, ethanol, and an acid catalyst Acetic anhydride and ethanol Sodium acetate and ethanol Sodium acetate and ethyliodidearrow_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_forwardBenzo(a)pyrene is a well known carcinogen. Based on its chemical properties, explain why benzo(a)pyrene and similar compounds are dangerous mutagens.arrow_forward
- Define the Properties of Epoxides ?arrow_forwardShow 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.arrow_forwardIn the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid diethylamide (LSD): మగవా జి N-H LSD (CH25N;O) Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD? pH =arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning