7. An unknown amine X has the molecular formula C8H₁7N. Treatment of amine X with excess CH31 followed by Ag₂O and heat afford only a mixture of two isomeric unknown amines Y and Z, each with the molecular formula C9H19N (indicating one DUS). Treatment of the mixture of Y and Z with excess CH3l, Ag₂O and heat afforded the following dienes along with N(CH3)3: 从从 -1 Unknown amine X has only four peaks in its 13C NMR spectrum and no peaks greater than 3000 cm-¹ in its IR spectrum. What are the structures of X, Y and Z?

7. An unknown amine X has the molecular formula C8H₁7N. Treatment of amine X with excess CH31 followed by Ag₂O and heat afford only a mixture of two isomeric unknown amines Y and Z, each with the molecular formula C9H19N (indicating one DUS). Treatment of the mixture of Y and Z with excess CH3l, Ag₂O and heat afforded the following dienes along with N(CH3)3: 从从 -1 Unknown amine X has only four peaks in its 13C NMR spectrum and no peaks greater than 3000 cm-¹ in its IR spectrum. What are the structures of X, Y and Z?

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

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.55P

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Compounds A, B, and C have the same molecular formula C4H8. They all react wotu H2/PtO2 to give the same compound. The reaction of A or B with H2O/H2SO4 or with BH3-THF, followed by treatment with a basic solution of hydrogen peroxide, gives the same compound, namely D. The reaction of C with H2O/H2SO4 also gives D. However, the reaction of C with BH3-THF, followed by HO-, H2O2 gives a new compound, E. Provide the identity of A, B, C, D, and E along with explanations of reactivity.
The treatment of (CH3)2C = CHCH2Br with H2O forms B (molecular formula C5H10O) as one of the products. Determine the structure of B from its H NMR and IR spectra.
Benzonitrile (C6H5CN) is reduced to two different products depending on the reducing agent used. Treatment with lithium aluminum hydride followed by water forms K, which has a molecular ion in its mass spectrum at 107 and the following IR absorptions: 3373, 3290, 3062, 2920, and 1600 cm-1. Treatment with a milder reducing agent forms L, which has amolecular ion in its mass spectrum at 106 and the following IR absorptions: 3086, 2820, 2736, 1703, and 1600 cm-1. L shows fragments in its mass spectrum at m/z = 105 and 77. Propose structures for K and L and explain how you arrived at your conclusions.
Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H₂O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data? a. Isomer A is cyclopentene and isomer is 1-pentyne O b. Isomer A is cyclopentene and isomer B is 1-methylcyclobutene c. Isomer A is cyclopentene and isomer B is 3-methylcyclobutene d. Isomer A is 1-methylcyclobutene and isomer B is 3-methylcyclobutene
Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. What is the isometric pair of A and B that corresponds?
Two isomers, A and B, of molecular formula C5H8 undergo catalytic hydrogenation with hydrogen gas and palladium on carbon to form the same C5H10 product. On ozonolysis followed by treatment with hydrogen peroxide (H2O2), isomer A gave a product of molecular formula C5H8O4 that has two carboxylic acid groups in it whereas isomer B gave a product of molecular formula C5H8O3 that contains a carboxylic acid group and a ketone group. Which of the following isomeric pairs best match this data?
The treatment of (CH3)2C=CHCH2Br with H2O forms B (molecular formulaC5H10O) as one of the products. Determine the structure of B from its 1H NMR and IR spectra.
Treatment of benzoic acid (C6H5CO2H) with NaOH followed by 1-iodo-3methylbutane forms H. H has a molecular ion at 192 and IR absorptions at 3064, 3035, 2960−2872, and 1721 cm−1. Propose a structure for H.
Deduce the structures of compounds A and B, two of the major components of jasmine oil, from the given data. Compound A: C9H10O2; IR absorptions at 3091–2895 and 1743 cm-1; 1H NMR signals at 2.06 (singlet, 3 H), 5.08 (singlet, 2 H), and 7.33 (broad singlet, 5 H) ppm. Compound B: C14H12O2; IR absorptions at 3091–2953 and 1718 cm-1; 1H NMR signals at 5.35 (singlet, 2 H) and 7.26–8.15 (multiplets, 10 H) ppm.
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