3 Treatment of 1-aminoadamantane, C„H„N, with methyl 2,4-dibromobutanoate in thepresence of a nonnucleophilic base, R,N, involves two successive S,2 reactions and givescompound A. Propose a structural formula for compound A.R&NNH, + Br.C15H93NO, + 2 R,NH BrOCHBr1-AminoadamantaneMethyl2,4-dibromobutanoateA

In the given SN2 reaction, 1-aminoadamantane act as a nucleophile and it make a bond with terminal…

Answered: 3 Treatment of 1-aminoadamantane,…

Organic Chemistry

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Author:John E. McMurry

Publisher:John E. McMurry

Chapter23: Carbonyl Condensation Reactions

Section23.SE: Something Extra

Problem 33MP: Azlactones are important starting materials used in the synthesis of dehydro Î±-aminoacids. They...

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ArCN MeMgl Et₂O/C6H6 HN Ar NaBH3CN, AcOH H₂N Ar 8 6 Scheme 4: Preparation of [(9-anthryl)alkyl]- and (mesitylalkyl)amines 6h and 6j from nitriles via imines 8.
Answer Q89, 90, 91
Draw a resonance structure of the acetonitrile anion, -: CH2CN, and account for the acidity of nitriles.
As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich WĂ¶hler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone. (a) What is a likely structure for the keto acid? (b) What is a likely structure for ecgonine, neglecting stereochemistry? (c) What is a likely structure for cocaine, neglecting stereochemistry?
Amino acids can be prepared by reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. Show how you would prepare alanine, CH3CH(NH2)CO2H, one of the twenty amino acids found in proteins, and propose a mechanism for acid-catalyzed conversion of the initial alkylation product to the amino acid.
The polyurethane foam used for home insulation uses methane-diphenyldiisocyanate (MDI) as monomer. The MDI is prepared by acid-catalyzed reaction of aniline with formaldehyde, followed by treatment with phosgene, COCl2. Propose mechanisms for both steps.
Nitriles, Râ€“=Câ‰¡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2Câ‰¡N, if it has IR absorptions from 2500â€“3100 cm-1 and at 1710 cm-1, and has M+=74?
Propose a reagent for the conversion of B to C.
Heating compound X with aqueous formaldehyde forms Y (C17H23NO), which has been converted to a mixture of lupinine and epilupinine, alkaloids isolated from lupin, a perennial ornamental plant commonly seen on the roadside in parts of Alaska. Identify Y and explain how it is formed. HO но CH=0 one step NH2 C,,H23NO lupinine epilupinine Ph
H₂C ཏཱཏི 1 ནི OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br2 in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions :0: H3C Br Br + :::OH2 Br H₂O H3C Br за
Propose an efficent synthesis.
Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.

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