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

Chapter24: Amines And Heterocycles

Section24.SE: Something Extra

Problem 44MP

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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.
1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C H₁C CO₂Et CO₂H CO2 + EtOH The malonic ester synthesis is a carbonyl alkylation reaction. It is used to prepare carboxylic acids from primary alkyl halides, lengthening the carbon chain by two atoms. Thus, the product can be visualized as being a "substituted acetic acid." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions EtO₂C X ¯:0: :0: Br: EtO₂C. Br CH3 H3C CH3 CH3 56
Show how the synthetic scheme developed in Problem 23.67 can be modified to synthesize this triiodobenzoic acid X-ray contrast agent.
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
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
1. NaOEt CO₂Et 2. H3O+ 3. heat Br H3C CO₂H CO2 H3C CO₂Et The malonic ester synthesis is a carbonyl alkylation reaction. It is used to prepare carboxylic acids from primary alkyl halides, lengthening the carbon chain by two atoms. Thus, the product can be visualized as being a "substituted acetic acid." The reaction consists of three steps: generation of the enolate anion followed by SN2 reaction with a primary alkyl halide, ester hydrolysis under acid conditions, and decarboxylation. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 22 CX EtO₂C EtO₂C HOCH2CH3 HOCH2CH3 EtO₂C EtO₂C
From the table of available reagents select the one(s) you would use to convert butanoic acid to each of the following products:
Which of the following reagents will not undergo a substitution reaction with the benzenediazonium chloride salt.
Which reagents are best used to produce 4-methyl-2-pentanol from a ketone? a. amins and trace acid, followed separetely H2/PD/C b. sodium cyanide followed by HCl c. sodium borohydridd followed by acidic work up d. hydrogen cyanide followed by HCl e. none of the above

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