1. CNBr2. LiAlH43. H₂ONH22aPrimary 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 aminewith 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 InstructionsBrCEN:-C=N:Br

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Answered: 1. CN Br 2. LiAlH4 3. H₂O NH2 2a…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.47P

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based on this video: on Hinsberg Test Tests for Amines - MeitY OLabs (8.5min) https://www.youtube.com/watch?v=j5jgMUWri8U Write the reaction (two-step, in skeletal) of each test amine when tested in the Hinsberg Test.
2-cyanophenol (pka 7.0) is even more acidic than the 4-cyanophenol isomer. Propose an explanation of why it is so.
Account for the following :(i) Primary amines (R-NH2) have higher boiling point than tertiary amines (R3N).(ii) Aniline does not undergo Friedel – Crafts reaction.(iii) (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
(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?
Arrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine (b) Acetanilide, aniline, N-methylaniline (c) 2,4-Dichloroaniline, 2,4-dimethylaniline, 2,4-dinitroaniline (d) 3,4-Dichloroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline (e) Dimethylamine, diphenylamine, N-methylaniline
Starting with benzene, what is a possible product of this series of reactions?: 1) HNO3 & H2SO4 2) Fe, HCl 3) (CH3)2CH-Br, FeBr3 4) NaNO2, HCl, 0-10 oC 5) HBF4 2-fluoro-3-isopropylaniline m-fluoro-benzenesulfonic acid o-fluoro-isopropylbenzene 2-amino-benzenesulfonic acid
Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 3390–3400):
Phenol plus 1) 1/2 I2, HNO3; 2) Br2 + AlCl3; 3) HNO3/H2SO4; can yield ___________. 2-bromo-6-iodo-4-nitrophenol 1-bromo-3-iodo-4-amino-phenol 3-bromo-5-iodo-4-nitrobenzene 2-bromo-3-iodo-4-hydroxy-aniline 2-bromo-3-iodo-4-nitrophenol
Draw the products formed when p-methylaniline (p-CH3C6H4NH2) is treated with each reagent. a. HCl b. CH3COCl c. (CH3CO)2O d. excess CH3I e. (CH3)2C = O f. CH3COCl, AlCl3 g. CH3CO2H h. NaNO2, HCl i. Part (b), then CH3COCl, AlCl j. CH3CHO, NaBH3CN
Aziridines are heterocycles that contain an N atom in a three-membered ring. Like epoxides, aziridines are strained and reactive because the 60° bond angles of the three-membered ring deviate greatly from the theoretical tetrahedral bond angle. One step in the synthesis of the drug oseltamivir (trade name Tamiu, Section 3.2) involves the conversion of amine X to diamine Y, a reaction that occurs by way of an intermediate aziridine. Draw a stepwise mechanism for the conversion of X to Y. Indicate the structure of the aziridine intermediate, and explain the trans stereochemistry of the two amines in Y.
Draw the products formed when p-methylaniline (p-CH3C6H4NH2) is treated with each reagent.a. HClb. CH3COClc. (CH3CO)2Od. excess CH3Ie. (CH3)2C = Of. CH3COCl, AlCl3g. CH3CO2Hh. NaNO2, HCli. Part (b), then CH3COCl, AlCl3j. CH3CHO, NaBH3CN
i) 3-methyloctane-2,3-diol 11) 3-chloro-4-ethoxy-2-methylcyclopentanamine iii) N, N, 3,3-tetramethylbutan-2-amine iv) 1-ethoxy-2,5-difluorohexan-3-ol 6) 5-isopropoxy-3-isopropyl-6-propoxy-4-propylcyclohexane -1, 2-diol draw of the following names in skeletal forms

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