The following retrosynthesis is correct. [You should consider the reactions (alkylation, Gabriel, azide, and reductive amination) presented for the synthesis of amines when answering this question.] True False N I-Z H NH3 H (x2)
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- Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide with azide ion (-N3), followed by catalytic hydrogenation. (Hint: An alkyl azide is not nucleophilic.)Self Study/Amines-Reactions Name: 1) Show how m-toluidine (shown on the right) can be converterd to the following compounds using any neccesary reagents. (You can use a previously synthesized compound to carry on). H3C. NH2 a) H3C CN m-toluonitrile H3C. b) CH,NH2 H3C. m-iodotoluene OH d) HC. m-cresolb)Congo Red indicator is synthesized via coupling reaction of diazonium salt which is obtained by the reaction of a primary amine and nitrous acid at 0°C. Draw the structures of the starting materials for the synthesis in the boxes. HO;S SO3 N- OH N- NH2 H2N Congo Red Diazonium salt Amine derivative
- Draw the possible stereoisomers of 2-methylocta-4,6-dien-1-amine. Note that E-, Z- isomers of each stereoisomer are also possible and would not be accounted for by the formula above; draw any E- or Z- isomers.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*, H20Stan and Kyle have observed a reaction between the aniline derivative A and acetone. a) Stan believes the product made is the imine B, whereas Kyle believes the aminal C was synthesized instead. Based on your technical expertise of organic chemistry gathered so far, how would you empirically determine which of the two boys is more likely to be correct, assuming you don't have access to pure samples of B and C? Be specific. TTAA NH2 CI В Aniline Imine Aminal
- use your knowledge of acid-base extraction to come up with a plan to separate the following compounds from each other. Your plan should include specific solvents or reagents to be used and result in 4 isolated solids in the end. p-anisidine pyrene salicylic acid: 2,3-xylenol *Here is an hint and example: p=Anisidine is an amine, xylenol is a phenol, and salicylic acid has COOH and phenol groups. Always start with identifying the functional groups and you either add acids or bases to react then after you get your layer, you extract and normally you will get precipitation at the bottom and you collect it by vacuum iteration, solate the amine by extracting with HCl. The ammonium salt will be in the aqueous layer. Neutralize it by adding base (NaOH) until the solution is basic. Collect the amine(which we expect to precipitate) by vacuum filtration.(1) Which is the most basic amine and which is a secondary amine? (2) Which can undergo hydrolysis? (3) Which gives a diazonium salt upon reaction with HNO2, HCl at 0oC?There are three steps in Somfai's short synthesis of the alkaloid, stemoamide. Supply the missing reagents and products in this three-reaction sequence in the middle of the synthesis. H. 1) I-B: BRZNCH2CO2ET Grubbs-II P Q R CH2CI2 (Ph3P)4Pd THF-DMPU, A 2) НОАС C11H16|NO C15H23NO3 C13H19NO3
- Several 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.(a) allyl bromide S allylamine (b) ethylbenzene S p@ethylanilineQ5:- Give structures and names of the principal organic reactants and products of the following reactions. a- pentinoic acid from butanol b- Preparation of acid anhydrides Q6:- Rank the following substances in order of increasing acidity , Justify your choice. benzoic acid, p-chlorobenzoic acid , 2,4-dichlorobenzoic acid , 2,4,6-trichlorobenzoic acidAnswer the following questions based on the information provided. (b) 1. SOCI2 OH 2. NaN3, heat 3. ELOH draw the products after the first and second step after 1st step after 2rd step ii) why does not the reaction afford the amine as final product? Explain it by drawing the mechanism of final step IZ