Starting with 2-methylpropene and using any other needed reagents, outline a synthesisof TWO from the following:a. (CH3)3COHb. (CH3)3CBrc. (CH3)2C(OH)CH2Cl7. Three compounds A, B, and C all have the formula C6H10. All three compoundsrapidly decolorize bromine in CC14; all three are soluble in cold concentrated sulfuricacid. Compound A has an absorption in its IR spectrum at about 3300 cm, butcompounds B and C do not. Compounds A and B both yield hexane when they aretreated with excess hydrogen in the presence of a platinum catalyst. Under theseconditions C absorbs only one molar equivalent of hydrogen and gives a product with theformula C6H12. When A is oxidized with hot basic potassium permanganate and theresulting solution acidified, the only organic product that can be isolated is CH3(CH2)3CO2H. Similar oxidation of B gives only CH3CH2CO₂H, and similar treatment of Cgives only HO2C(CH2) 4CO2H. What are the structure for A, B, and C?11

7. In order to determine the structure of compounds A, B, and C, we need to consider the following…

Answered: Starting with 2-methylpropene and using…

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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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
1. The sex attractant for the common housefly is a hydrocarbon with the molecular formula C23H46. On treatment with KMNO4, two products are formed: CH3(CH2)2CH(CH(CH3)2)- (CH2)6CO2H and (CH3)3C-(CH2)4-CO2H. Propose TWO structures for this sex attractant.
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently with D2O to give 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 reacts with 2 equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess H2 and Pt catalyst to give 2-methylpropylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.
Compound A (C7H11Br) is treated with magnesium in ether to give B (C7H11MgBr), which reacts violently with D2O to give 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 H2 SO4 gives E (C10 H16), which decolorizes two equivalents of Br2 to give F (C10H16 Br4). E undergoes hydrogenation with excess H2 and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F, and show your reasoning throughout.
2-bromo-2-methylbutane undergoes hydrolysis reaction with water, H2O toform compound W. Compound X and compound Y are produced when 2-bromo-2-methylbutane undergoes elimination reaction with alcoholic ofsodium hydroxide, NaOH. (i) Draw the structural formula of compounds W, X and Y
18. Compound A (C7H₁1Br) is treated with magnesium in ether to give B (C7H11MgBr) which reacts violently with D2O to give 1-methylcyclohexene with a deuterium atom on the methyl group (C). Reaction of B with acetone followed by hydrolysis gives D (C10H180). Heating D with concentrated H2SO4 gives E (C10H16), which decolorizes two equivalents of Br2 to give F (C10H16Br4). E undergoes hydrogenation with excess of H₂ and a Pt catalyst to give isobutylcyclohexane. Determine the structures of compounds A through F by showing clearly all the reactions involved.
Benzene, C6H6 undergoes substitution reaction with concentrated nitricacid, HNO3 to produce compound L. The reaction of compound L withbromine, Br2 in the presence of iron tribromide, FeBr3 produced compoundM. Benzene also undergoes Fridel-crafts alkylation reaction withchloroethane, CH3CH2Cl using catalyst N to produce compound P (i) Draw the structural formula of L, M and P (ii) State catalyst N. (iii) Show the formation of electrophile that will be reacted with benzene for theformation of compound P.
Cyclopentene reacts with reacts with ozone in dichloromethane at -78° C. Treatment of the resulting ozonide with zinc in acetic acid or with dimethylsulfide gives A(C3H3O2). Treatment of A with sodium borohydride in ethanol gives B(C3H12O2). Draw the structure of B.
(S)-2-butanol reacts with potassium dichromate (K2CrO4) in aqueous sulfuric acid to give A(C,HgO). Treatment of A with ethylmagnesium bromide in anhydrous ether gives B(C,H140). Draw the structure of B.
Compound C has the molecular formula C;H12. On catalytic hydrogenation, 1 mol of C absorbs 1 mol of hydrogen and yields a compound with the molecular formula C7H14. On ozonolysis and subsequent treatment with zinc and acetic acid, C yields only: The structure of C is:
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. Which of the following isomeric pairs best match this data?

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