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
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- 1. Show the products of the reductive amination reactions below; a) Acetone + NH3, followed by H2/Ni2 b) Acetone + CH3NH2, followed by LIBH3CN c) Acetone + (CH3)2NH, followed by LIBH3CN 2. Write the reaction and the names of the products formed in the reaction of aniline and N-methylaniline with: a) NaNO3+HCI followed by CuClI b) NaNO3+HCI followed by Cu20, Cu2*, H20Give the major product for the reaction. Pyrrolidine is a secondary amine. CH CH O CH CH! O OH CH2 O CH. I CH.CH Ї TCH CHE OH CH CH₂CH₂ CH.CH CH.OH2 0= RO pyrrolidine. 2 GH CH2 3 HCI H,0 TOH OH: CH₂CH₂ TCH CH: CH₂CH. CH₂CH₂NOC 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 8b
- 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 BrO NaBH4 Synthesis #2: Select a different set of two substrates and one reagent that could be combined to prepare benzphetamine. tymen Ph Ph Ph Ph NH Ph H O NaBH3CN, H+ 20= ano [H*], NaBH-CN NucleophileSeveral 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@amine
- 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 заState all the products formed from Hofmann elimination of the following amine. Choose the major product. Show the mechanism to obtain the major product. а. b. с. NH2 CH,CHCH3 NH2 NH2Br 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
- 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.Primary amines can be converted into secondary amines by reaction with haloalkanes. This reaction is difficult to achieve in the lab because of the large number of byproducts. Select the possible products or byproducts of the reaction. H3C-NH2 The products and `Br byproducts are: (1 equiv) (1 equiv) O B D Bre HN CH, O I E A B D F Br H Br O O K E O Br O OG O A J K O O O O O O O OIn the Gabriel synthesis of primary amines, N-potassiophthalimide is used as a source of the nitrogen atom. Complete the synthesis reactions by drawing the missing structures. Ignore inorganic counterions. NH2 N K* DMF Step 1 Product NaOH (xs) H2O, heat Step 2 Product Br KBr