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 And Biological Chemistry

7th Edition

ISBN:9781305081079

Author:STOKER, H. Stephen (howard Stephen)

Publisher:STOKER, H. Stephen (howard Stephen)

Chapter3: Alcohols, Phenols And Ethers

Section: Chapter Questions

Problem 3.71EP

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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
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
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.
(S)-2-butanol reacts with potassium dichromate (K2CrO4) in aqueous sulfuric acid to give A(C4H3O). Treatment of A with ethylmagnesium bromide in anhydrous ether gives B(C,H140). Draw the structure of B.
An optically active alkyne A (C10H14) can be catalytically hydrogenated to butylcyclohexane. Treatment of A with EtMgBr liberates no gas. Catalytic hydrogenation of A over Pd/C in the presence of quinoline poison and treatment of the product with O3 and then H2O2 gives an optically active tricarboxylic acid C8H12O6 (A tricarboxylic acids is a compound with three - CO2H groups.). Give the structure of A, and account for all observations.
1) (S)-2-butanol reacts with potassium dichromate (K2CrO4) in aqueous sulfuric acid to give A (C4H8O). Treatment of A with ethylmagnesium bromide in anhydrous ether gives B (C6H14O). Draw the structure of B. 2)
-Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.
Compound A has the formula C₂H₁9Cl. B is a C₂H19Br compound. A and B undergo base-promoted E2 elimination to give the same alkene C as the major product as well as different minor products. C reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2,6-dimethylheptane. Addition of HCI to C yields A as the major product. Propose structures for A and B. • Do not use stereobonds in your answer. • In cases where there is more than one possible structure for each molecule, just give one for each. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. ● ▾ *%-85 ChemDoodle Qt Jn [F 116

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