3 Treatment of 1-aminoadamantane, C„H„N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R,N, involves two successive S,2 reactions and gives compound A. Propose a structural formula for compound A. R&N NH, + Br. C15H93NO, + 2 R,NH Br OCH Br 1-Aminoadamantane Methyl 2,4-dibromobutanoate A
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- An amine of unknown structure contains one nitrogen and nine carbon atoms. The 13C-NMR spectrum shows only five signals, all between 20 and 60 ppm. Three cycles of Hofmann elimination sequence [(1) CH3I; (2) Ag2O, H3O; (3) heat] give trimethylamine and 1,4,8-nonatriene. Propose a structural formula for the amine.4. Here’s a figure-it-out mechanism, resulting in the formation of p-aminophenol from an aromatic hydroxylamine. Would you expect either ortho- or meta-aminophenol to form in competition? Why or why not? H H;0* H -N НО H2O ОН H 5. (a) The triaryl hydroxylamine hydrolyzes in acid to form two products: one compound containing two aromatic rings and one with a single aromatic ring. First, draw the two products and the mechanism of their formation in acidic water (this is another "figure it out" mechanism). Ph H;O* Ph—С—N H,0 Ph ОН (b) Suppose one of the aryl rings had a t-donating group (-OCH3) and the other had a n- withdrawing group (-NO2), both in the para position. Where would the substituents end up in the products (draw them)? Why? Do you suspect this reaction is under kinetic control or thermodynamic control, or both/either?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 Wöhler 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.Nitriles, R–=C≡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the structure of the compound produced by hydrolysis of propanenitrile, CH3CH2C≡N, if it has IR absorptions from 2500–3100 cm-1 and at 1710 cm-1, and has M+=74?
- 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.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 PhH₂C 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
- [24166 Ji 10201900 (c) Propose reagents and conditions for the following 3-step synthesis of secondary amine 10, starting from azide 9. Your answer should include reagents and conditions for all three steps and a full curly arrow mechanism for the benzylation step (i.e. from primary amine 11 to secondary amine 12). Comment on any predicted selectivity. N3 m obydob is 10 br 9, 0-0 25 ilqmoxs of ozonit o = =Et Isaiavda se ni tons 3 steps Benzylation step: bre quotesmotional sies no H₂NY 11:0g 00S - (0=01 BOYH2OJA 0-3168 A3T23 ZI N H ZI H 12 10 wwww -EtReaction of acetic acid, CH3CO2H, with isotopically labeled CH318OH and catalytic sulfuric acid gives: 180 A) CH;COCH; + H2O CH;C "OCH; + H,0 180 II C) CH;COCH3 + H¿®O D) equal amounts of A and BTreating trimethylamine with 2-chloroethyl acetate gives acetylcholine as its chloride. Acetylcholine is a neurotransmitter. Me;N + CH,COCH,CH,CI C,H1,CINO, Acetylcholine chloride Propose a structural formula for this quaternary ammonium salt and a mechanism for its formation.