Interpretation:
A detailed mechanism for the reaction between compound designated as “2” and ethyl acetoacetate in the presence of ethoxide ion to form the given product is to be written.
Concept introduction:
Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.
Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.
Free radical is an atom, molecule, or ion that has unpaired electrons that makes it highly chemically reactive.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
Carbonyl condensation usually involves reaction of two carbonyl groups to join both of the reactants. Claisen condensation is a
An intermolecular Claisen condensation is called a Dieckmann condensation. This type of condensation reaction is useful in the preparation of five or six membered rings.
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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_forwardH NH₂ ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩ H NH3+ the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product. the resulting carboxylic acid ion is a weaker base than an acetate ion. O aldehydes are more reactive toward nucleophiles than ketones. Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.arrow_forwardOn the basis of the general mechanism for acid-catalyzed ester hydrolysis shown in Mechanism 20.2, write an analogous sequence of steps for the specific case of ethyl benzoate hydrolysis.arrow_forward
- Nifedipine (Procardia and Adalat) belongs to a class of drugs called calcium channel blockers 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 to Problems 19.43 and 19.54 and then combine that chemistry to solve this problem.) NO COOME MEOOC, acid + 2 `NO2 OMe +NH3 СНО H Nifedipinearrow_forwardDiazepam, better known as Valium, is a central nervous system (CNS) sedative/ hypnotic. As a sedative, it diminishes activity and excitement and thereby has a calming effect. Back in 1976, based on the number of new and refilled prescriptions processed, diazepam was the most prescribed drug in the United States. Following is a retrosynthetic analysis for a synthesis of diazepam. Note that the formation of compound B involves a Friedel-Crafts acylation. In this reaction, it is necessary to protect the 2° amine by prior treatment with acetic anhydride. The acetyl-protecting group is then removed by treatment with aqueous NaOH followed by careful acidification with HCl. Q.Given this retrosynthetic analysis, propose a synthesis for diazepamarrow_forwardDiazepam, better known as Valium, is a central nervous system (CNS) sedative/ hypnotic. As a sedative, it diminishes activity and excitement and thereby has a calming effect. Back in 1976, based on the number of new and refilled prescriptions processed, diazepam was the most prescribed drug in the United States. Following is a retrosynthetic analysis for a synthesis of diazepam. Note that the formation of compound B involves a Friedel-Crafts acylation. In this reaction, it is necessary to protect the 2° amine by prior treatment with acetic anhydride. The acetyl-protecting group is then removed by treatment with aqueous NaOH followed by careful acidification with HCl. Q. Is diazepam chiral? If so, how many of the possible stereoisomers are formed in this synthesis?arrow_forward
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