Br1. N32. LiAlH43. H₂ONH₂26Preparation of primary amines using azide ion avoids the problem of over-alkylation since the alkyl azide is not nucleophilic. The alkyl azide is prepared from an alkyl halide via an SN2 reaction with N3as the nucleophile. Subsequent reduction of the azide with LiAlH4 leads to the desired amine.Draw curved arrows to show the movement of electrons in this step of the mechanism.Arrow-pushing InstructionsH|-H-AI-HHH1Al.H

Answered: Br 1. N3 2. LiAlH4 3. H₂O NH₂ 26…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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1. CN Br 2. LiAlH4 3. H₂O NH2 2a Primary amines can be prepared from nitriles by reduction with LiAlH4. The two-step sequence involves SN2 displacement of halide ion by cyanide ion followed by reduction, and yields a primary amine with one more carbon than was present in the alkyl halide. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br CEN: -C=N: Br
H3C 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 Br Br зь P-Br Br H₂C H₂C SH Br Br
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.
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Amino acids can be prepared by the reaction of alkyl halides with diethyl acetamidomalonate, followed by heating the initial alkylation product with aqueous HCl. The reaction to form alanine involves the following steps: Reaction of diethyl acetamidomalonate with sodium ethoxide to form enolate anion 1; The enolate anion acts as a nucleophile in an SN2 reaction with alkyl iodide 2 to form alkylated intermediate 2; Heating in the presence of aqueous acid hydrolyzes both the ester and the amide bonds, and induces decarboxylation to form alanine. Draw the structure of enolate anion 1.
H3C. 00 H3C. CH3 XII HO: OCH3 Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 2 CH₂OH HCI catalyst CH3 H3C H-OH₂ H3CO OCH3 CH3 H3C. H₂O: OCH3 CH3 H₂O Ча
Propranolol, an antihypertensive agent used in the treatment of high blood pressure, can be prepared from 1-naphthol, epichlorohydrin, and isopropylamine using two successive nucleophilic substitution reactions. Devise a stepwise synthesis of propranolol from these starting materials.
Show how the synthetic scheme developed in Problem 23.67 can be modified to synthesize this triiodobenzoic acid X-ray contrast agent.
G.230.
1. CN Br 2. LIAIH4 3. H₂O σ NH2 Primary amines can be prepared from nitriles by reduction with LiAlH4. The two-step sequence involves SN2 displacement of halide ion by cyanide ion followed by reduction, and yields a primary amine with one more carbon than was present in the alkyl halide. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions X 2- H-OH NH + OH 2 C
1. Br₂, PBrg 2. H₂O H₂C OH 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 α- 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 H3C :0: :0::Br: Br Br H3C CO-P H Br Br
Amoxycillin is often adminisstered as the sodium salt. It is more soluble form that results from the reaction: Amoxycillin + NaOH --> Sodium-amoxycillin + H2O What functional grouo omn amoxycillin allows it to act as an acid in the reaction?

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