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 functional group is substituted by any other functional group is called substitution reaction.
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 CHEM. VOL.1+2-W/WILEYPLUS
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- Paroxetine (Paxil) is an antidepressant that is a member of a family of drugs known as Selective Serotonin Reuptake Inhibitors (SSRIS). This family of drugs also includes fluoxetine (Prozac) and sertraline (Zoloft). SSRIS work by inhibiting the reuptake of the neurotransmitter serotonin in the synapses of the central nervous system follow- ing release of serotonin during excitation of individual nerve cells. Between firings, the serotonin is taken back up by a nerve cell in preparation for firing again. Inhibition of reuptake has the effect of increasing the time serotonin molecules remain in the syn- apses following excitation, leading to a therapeutic effect. In one synthesis of parox- etine, the following reagents are used. Draw the structures of synthetic intermediates A and B. F НО SOCI, A B HO Pyridinearrow_forwardA 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_forwardNifedipine (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_forward
- Which of the following best represents a mechanistic step in the acid-catalyzed hydrolysis of acetonitrile? А) НС —СEN: Н-ӧ: Н В) НС —СN-H Н-ӧ: н С) НС —СN: н ӧ: D) H3C-C=N: Н-ӧ: нarrow_forward5. The target compound below (a potential ẞ-blocker drug) may be prepared using a sulfonium ylide (and then a 2° amine) according to the retrosynthetic scheme shown below. Please perform the following: (a) Draw the structure of a suitable ylide that would accomplish this task and (b) write a mechanism to depict the formation and subsequent usage of the ylide (for the reaction in which the aldehyde is converted into the epoxide)...so the mechanism does NOT have to include the amine + epoxide part of the synthesis. HO NR2 1-8 potential class of ẞ-blocker drugs sulfonium ylide Harrow_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_forward
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