15.27 Starting with aniline, outline a synthesis ofeach of the following:(a) p- Bromoaniline(c) 2 Bromo-4-nitroaniline-(e) 2,4,6-Tribromoaniline(b) o Bromoaniline-(d) 4 Bromo-2 - nitroaniline-15.27 Starting with aniline, outline a synthesis ofeach of the following:(a) p- Bromoaniline(c) 2 Bromo-4-nitroaniline-(e) 2,4,6-Tribromoaniline(b) o Bromoaniline-(d) 4-Bromo-2 - nitroaniline

General Considerations:Aniline is a strongly activating, ortho/para-directing group due to the…

Answered: 15.27 Starting with aniline, outline a…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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19.24b Show how you would synthesize the below compound from 1,2,5-pentanetriol OH OH HO (b)
Indicate the order of basicity of: aniline, 2-propylamine and 1-(2-aminophenyl)ethanone. Explain.
[8] Which compound when treated with acid and or heat would yield following ČH3 (a) hexanoic anhydride (b) 4-hydroxy-3,3-dimethylbutanoic acid (c) 4-hydroxy-4-methylpentanoic acid (d) 5-hydroxyhexanoic acid (e) 6-hydroxyhexanoic acid
8
(c) The sedative, R-thalidomide, was once used to address symptoms of morning sickness in expectant mothers, however, when it was discovered that S- thalidomide causes deformities in infants, the use of R-thalidomide as a sedative was discontinued. With the help of a reaction mechanism, explain why enantiopure R-thalidomide can not be safely used as a sedative without affecting infants
1
13. (a) Compound C undergoes a reaction with SOC1₂ (or PC15) to yield compound D (Molecular Formula C₁0H₁0OCIBr) which has the following spectral data: Compound D: IR: 1685 cm¹; ¹H NMR: 8 7.84 (d, J = 8 Hz, 2H), 7.60 (d, J=8 Hz, 2H), 3.65 (t, J = 7 Hz, 2H), 3.18 (t, J = 7 Hz, 2H), 2.25 (pentet, J = 7 Hz, 2H) ppm; ¹3C NMR: d 28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200, 198(1:1), 185, 183 (1:1). Identify compound C from the spectral data of compound B and justify your observation. (b) Differentiate between the following: i) COSY and NOESY ii) COSY 90 and COSY 45
1.4) Provide a retrosynthetic analysis for the following compound and show how you would synthesize it from aryl starting materials.
10.30 Provide the reagents necessary for the following synthetic transformations. More than one step may be required. (a) OH (b) Br (c) OH (d) (e) (f) LOCH3 Br Br
13. (a) Compound C undergoes a reaction with SOC12 (or PCls) to yield compound D (Molecular Formula C₁0H₁0OCIBr) which has the following spectral data: Compound D: IR: 1685 cm¹; ¹H NMR: 8 7.84 (d, J = 8 Hz, 2H), 7.60 (d, J = 8 Hz, 2H), 3.65 (t, J = 7 Hz, 2H), 3.18 (t, J = 7 Hz, 2H), 2.25 (pentet, J = 7 Hz, 2H) ppm; ¹³C NMR: d 28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200, 198(1:1), 185, 183 (1:1). Identify compound C from the spectral data of compound B and justify your observation.
2. (a) Ozonolysis of compound A, C,H12 gave two products B and C. Further analysis of these two compounds of B and C, showed positive results with 2,4-dinitrophenylhydrazine. Compound B reacts with Tollens' reagent while compound C does not indicate any positive result to the same reagent. However, both B and C gave same positive results with iodoform test. (i) By writing all the chemical equations involved, identify A, B and C.
Detailed mechanism of reaction of compound 5 with phosphorous tribromide to give compound 3

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