Unknown X, C5H9BrC5H9Br, does not react with bromine or with dilute KMnO4KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C5H8C5H8. Unlike X, Y decolorizes bromine and changes KMnO4KMnO4 from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis-reduction of Y gives dialdehyde Z, C5H8O2C5H8O2. Part A Propose consistent structures for X, Y, and Z.

Unknown X, C5H9BrC5H9Br, does not react with bromine or with dilute KMnO4KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C5H8C5H8. Unlike X, Y decolorizes bromine and changes KMnO4KMnO4 from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis-reduction of Y gives dialdehyde Z, C5H8O2C5H8O2. Part A Propose consistent structures for 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

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.15P

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Part A

Propose consistent structures for X, Y, and Z.

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Unknown X, C5H9Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide,X gives only one product, Y, C5H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown.Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C5H8O2. Proposeconsistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?
Cyclobutane fracts with bromine to give bromocyclobutane, but bicyclobutane reacts with bromine to give 1,3-dibromocyclobutane. Account for the differences between the reactions of thee two compounds.
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 1H NMR and IR spectra.
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.
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.
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?
In the following sequence of reactions which products are identified correctly? Compound A (C 7H 11B1) is treated with magnesium in ether to give B (C 7H 11MgBr), which reacts violently with D 20 to give 1-methylcyclohexene B with acetone (CH 3COCH 3) followed by hydrolysis gives D (C 10H 180). Heating D with with a deuterium atom on the methyl group C. Reaction concentrated H 2SO 4 gives E (C 10H 16), which decolorizes two equivalents of Br 2 to give F (C 10H 16Br 2). E undergoes hydrogenation with excess H 2 and a Pt catalyst to give isobutylcyclohexane. O The correct structure of C is OH O The correct structure of D is O The correct structure of C is Br OI The correct structure of F is 8r
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?
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O togive 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone (CH3COCH3)followed by hydrolysis gives D (C10H18O). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizestwo equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to giveisobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout
5. Please deduce the structures for following compounds. Compound A (C₂H₁002) works well in color reaction with FeCl3 solution. Compound A also can reaction with 2,4-dinitrophenylhydrozine but can't reaction with Tollens' reagent. Compound A was reduced with LiAlH, to product B (C₂H₁2O₂). Compound A and B both work well in iodoform reaction. Through Clemmensen reduction, Compound A was reduced to compound C (CH1202): Compound C was oxidized with KMnO, to form 4-hydroxybenzoic acid. Please draw out structures for compounds A, B and C and the reaction equations for all the transformation.
Q3] Diethyl malonate was treated with 2 moles of NaH followed by reaction with 1,4-dibromo-2-butene providing compound (A). Hydrolysis of compound A under heat 200 °C affording compound B; which was treated with PBr3 then with methanol/H+ affording C. The compound C then was exposed to ozonolysis conditions providing D. Finally two moles of ammonia react with D providing E. What are structures A..to .E?? A B C D E