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
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- 5. The acyl group is a protecting group for amines which can be deprotected by treatment with sodium hydroxide. Please write mechanisms for both the protection and deprotection steps. NaOH CH30-H NH2 protect deprotect R NH2 amine acetic anhydride N-acyl amineAmoxycillin 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?Br 1. N3 2. LiAlH4 3. H₂O NH₂ 26 Preparation 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 N3 as 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 Instructions H |- H-AI-H H H 1 Al. H
- 14. What products result from the reaction between water and the following amine: a. butyl ethyl methyl ammonium ion + OH+ b. butyl ethyl methyl ammonium ion + H3O+ c. butyl ethyl methyl ammonium ion + H3O d. butyl ethyl methyl ammonium ion + OH- e. butyl ethyl methyl ammonium ion + H2OSeveral additional amine syntheses are effectively limited to making primary amines. The reduction of azides and nitrocompounds and the Gabriel synthesis leave the carbon chain unchanged. Formation and reduction of a nitrile adds onecarbon atom. Show how these amine syntheses can be used for the following conversions. (c) 1@bromo@3@phenylheptane S 3@phenylheptan@1@amine (d) 1@bromo@3@phenylheptane S 4@phenyloctan@1@amineTreatment of 2-phenylpropan-2-amine with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. ? NH2 Br Br Propose a structural formula for compound A. You do not have to explicitly draw H atoms. You do not have to consider stereochemistry. In cases where there is more than one answer, just draw one. R3N C14H19NO2 + 2 R3NH*Br A
- H₂C 0 NH₂ B₂, NaOH 98 H₂C OH When an a-hydroxy amide is treated with try in aqueous NaOH under Hofmann rearrangement conditions, loss of CO, occurs and a chain-shortened aldehyde is formed. The mechanhum involves the following steps: Base abstracts an acidic amide proton, yielding amide anion The amide anion reacts with bromine in an e-substitution reaction to give N-bromoamide 2. Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion Rearangement occurs to yield isocyanate Water adds to the isocyanate to yield carbamic acid Elimination of CD, yields carbinolamine Following proton transfer, expubion of ammonia yields the final product aldehyde Write out the mechanism on a separate sheet of paper, and then draw the structures of carbamic acid 5 and isocyanate 4. H 400, ANH, You do not have to consider stereochemistry. You do not have to explicitly draw Hatoms De not include lone pairs in your answer. They will not be considered in the grading…Below is one of the reactions used in the synthesis of eluxadoline. What type of reaction is it? NABH, H,N catalytic amount HOAC MEOH, 5- 10 °C H,Co HN H,CO O Alkyation. Reductive amination. O Amide formation followed by reduction.Please don't provide handwritten solution.
- NOC XT Ph CH₂ Both primary and secondary amines add to a ß-unsaturated aldehydes and ketones to yield ß-amino aldehydes and ketones rather than the alternative imines. Under typical reaction conditions, both direct and conjugate modes of addition occur rapidly. But because the reactions are reversible, they generally proceed with thermodynamic control rather than kinetic control so the more stable conjugate addition product is often obtained to the complete exclusion of the less stable direct addition product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H H CH3NH₂ CH3 H-A :A Ph NHCH3 вон CH3 :A H-A 8b2262 Sat Aor 6 1 Which one of the following compounds is the strongest acid? CNH2 -NH2 -CO2H OH CI- СОН CH CH C A B 2. Which one of the following amines will not produce an amide when mixed with an acid chloride? NH PHCH,NH2 PHNH2 Et,NH A C 3. What is the major product of the following sequence of reactions? CH3 1) NBS, hv (excess) C(OH)3 CHO CO2H CH2O 2) NaOH, H20 (excess) A В C 4. What is the major product of the following intramolecular aldol condensation reaction? E NaOH H20 (dehydration) A C 3. D. BWhich of those would be formed? Then If the product of the reaction in the previous problem was subsequently mixed with sodium cyanoborohydride, which of the following would result? a. primary alcoholb. secondary alcohol c. primary amined. secondary amine e. tertiary amine