Gabapentin, an anticonvulsant used in the treatment of epilepsy, is structurally relatedto the neurotransmitter 4-aminobutanoic acid (GABA).-NH2-NH,B-СООНCOOHGabapentin4-Aminobutanoic acid(y-Aminobutyric acid, GABA)Gabapentin was designed specifically to be more lipophilic than GABA and thereforemore likely to cross the blood-brain barrier, the lipidlike protective membrane that sur-rounds the capillary system in the brain and prevents hydrophilic (water-loving) com-pounds from entering the brain by passive diffusion. Given the following retrosyntheticanalysis, propose a synthesis for gabapentin.-NH,-NH2CNCOOH-COOEtCOOEtGabapentinCOOEtCOOE.O +COOEtCOOEtCyclohexanoneDiethylmalonate

Retrosynthesis chemistry: It is part of chemistry that deals with disconnection approach in which…

Answered: Gabapentin, an anticonvulsant used in…

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 19.63P

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Heating toluene in the presence of KMnO4 followed by acification with HCl, converts toluene into benzoic acid. Using this information and any other reactions discussed in this course, show a sequence of reactions showing howing toluene can be converted to p-aminobenzoic acid.
The compound acetophenone has a very similar molar mass to that of benzoic acid and benzamide. However, acetophenone has a much lower m.p. (20 °C) than both such that, by contrast, it is a liquid at room temperature. By considering intermolecular forces and comparing functional group structure, account for this big difference in physical properties.
Give answers to these questions. Choose from the options A.The efficacy of salicylic acid as well as its solubility in water as compared to p-hydroxybenzoic acid is greatly affected by what phenomenon? Dipole moment Hydrogen bonding Ionic bonding Hydrophobic effect B.This is the most important CYP 450 isozyme that is responsible for the metabolism of almost 50% of the drugs available in the market CYP 2D6 CYP 2A9 CYP3A4 CYP 1A2 C.Ketones are oxidized into Aldehydes Carboxylic acid Secondary alcohol Unable to oxidized D.G- protein coupled receptors are activated via these secondary messengers, except cAMP DAG IP3 ATP E.The gas use for sterilizing heat labile substances Gluteraldehyde Ethylene oxide Nitrogen Acetylene
Aspirin, or 2-acetoxybenzoic acid, (C9H8O4) is often synthesised from salicylic acid.(i) Sketch and discuss any changes in the number of possible structural conformations ofaspirin relative to those of salicylic acid. (ii) Re-draw the structure predicted to be the lowest energy conformation of aspirin,indicating any expected stabilising and destabilising interactions. Justify your choice.
When the heterocycles pyridine (1) and pyrrole (2) are treated with the strong base methyllithium, pyrrole reacts to produce a lithium amide while pyridine does not react.
Can any functional groups on Risperidone ionize? If so, which ones? Under what conditions? What are the pKa values of these functional groups? Write the structures in their correct ionization state at physiological pH.
The pKavalues for glutathione are pKa1 =2.12 and pKa2 = 3.59 for successive deprotonation of the twoCOOH groups, pKa3 = 8.75 for the NH2 group, and pKa4 = 9.65 for the SH group. Predict the predominantform of GSH at the physiological pH of 7.4. Provide your predicted structure below
use your knowledge of acid-base extraction to come up with a plan to separate the following compounds from each other. Your plan should include specific solvents or reagents to be used and result in 4 isolated solids in the end. p-anisidine pyrene salicylic acid: 2,3-xylenol *Here is an hint and example: p=Anisidine is an amine, xylenol is a phenol, and salicylic acid has COOH and phenol groups. Always start with identifying the functional groups and you either add acids or bases to react then after you get your layer, you extract and normally you will get precipitation at the bottom and you collect it by vacuum iteration, solate the amine by extracting with HCl. The ammonium salt will be in the aqueous layer. Neutralize it by adding base (NaOH) until the solution is basic. Collect the amine(which we expect to precipitate) by vacuum filtration.
Treatment of salicylaldehyde (2-hydroxybenzaldehyde) with bromine in glacial acetic acid at 0°C gives a compound with the molecular formula C7H4Br2O2, which is used as a topical fungicide and antibacterial agent. Propose a structural formula for this compound
Starting with benzene, give a sequence of laboratory reactions which could be used to prepare p-isopropylaniline. If separation of ortho, meta, or para-isomers is required, give evidence that it is feasible.
The mechanism of the Fischer esterification was controversial until 1938, when IrvingRoberts and Harold Urey of Columbia University used isotopic labeling to follow thealcohol oxygen atom through the reaction. A catalytic amount of sulfuric acid was addedto a mixture of 1 mole of acetic acid and 1 mole of special methanol containing the heavy18O isotope of oxygen. After a short period, the acid was neutralized to stop the reaction,and the components of the mixture were separated.H2SO4OCH3 C O H CH3 O H CH3 C O CH3 H2OO18 + +(a) Propose a mechanism for this reaction.(b) Follow the labeled 18O atom through your mechanism, and show where it is found inthe products.(c) The 18O isotope is not radioactive. Suggest how you could experimentally determinethe amounts of 18O in the separated components of the mixture
Point out the hydrophilic and hydrophobic regions in the structures of benzalkoniumchloride, Nonoxynol®, and Gardol®

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