Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter FRP, Problem 13P
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Compound A has molecular formula C4H10. Compound A gives two monochlorides, B and C, on photochemical chlorination. Treatment of either of
these monochlorides with potassium tert-butoxide gives the same alkene (C4H8) as the product, but B leads to just one isomer of the alkene, D,
whereas C gives D and another isomer of the alkene, E. Treatment of monochlorides B and C with aqueous ethanol gives products F and G,
respectively, both of which are of molecular formula C4H100. What are the chemical names of compounds A-G?
4. Compound A has the formula C 8H 8. It reacts rapidly with KMnO 4 to give CO 2 and a carboxylic acid, B (C 7H 6O 2), but reacts with only 1 molar equivalent of H 2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H 2 are taken up and hydrocarbon C (C 8H 16) is produced. What are the structures of A, B, and C.
Compound A(C7H15Br) is not a primary alkyl bromide. It yields a single alkene(compound B) on being heated with sodium ethoxide in ethanol. Hydrogenation of compound B yields 2,4-dimethylpentane. Identify compounds A and B.
Chapter FRP Solutions
Organic Chemistry
Ch. FRP - Prob. 1PCh. FRP - 2. Which member of these pairs is the more polar?...Ch. FRP - 5. Though they each contain only one type of...Ch. FRP - Predict the products from each of the following...Ch. FRP - Prob. 5PCh. FRP - Prob. 6PCh. FRP - Prob. 7PCh. FRP - Prob. 8PCh. FRP - Predict the products from each of the following...Ch. FRP - Prob. 10P
Ch. FRP - 13. Starting with propyne and using any other...Ch. FRP - Bromination of 2-methylbutane yields predominantly...Ch. FRP - An alkane (A) with the formula C6H14 reacts with...Ch. FRP - Prob. 14PCh. FRP - Prob. 15PCh. FRP - Dehydrohalogenation of meso-1, 2-dibromo-1,...Ch. FRP - Prob. 17PCh. FRP - Prob. 18PCh. FRP - 27. (R)-3-Methyl-1-pentene is treated separately...Ch. FRP - Prob. 20PCh. FRP - Prob. 21PCh. FRP - Prob. 22PCh. FRP - Prob. 23PCh. FRP - Synthesize the following compound by a method that...Ch. FRP - Provide three methods that employ Grignard...Ch. FRP - 34. Compound Yexhibits one NMR signal at (a...Ch. FRP - Prob. 27PCh. FRP - 36. Compound X shows a strong IR absorption band...Ch. FRP - Prob. 29PCh. FRP - 38. In addition to more highly fluorinated...Ch. FRP - Fluorination of (R)-2-flurobutane yields a mixture...Ch. FRP - Prob. 32PCh. FRP - Prob. 33P
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- 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.arrow_forward2 methylbutene react with Hbr to givearrow_forwardCompounds A and B are isomers of the molecular formula CyH19Br. Both yield the same alkene Cin an elimination reaction. Hydrogenation of C yields the product 2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?arrow_forward
- An unknown compound, A, has the molecular formula C7H12. On oxidation with hot aqueous potassium permanganate, A yields CH3CH2COOH and (CH3)2 Which of the following structures best represents A?arrow_forwardAn alkene having the molecular formula C5H10 is treated sequentially with ozone (O3) and zinc/acetic acid to give the product/s shown. H3C O CH3CHCH + H. Draw a structural formula for the alkene. You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. In cases where there is more than one answer, just draw one. P opy aste [* Previous Nextarrow_forwardCompound 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.arrow_forward
- 5B In the following reactions, mixtures of alkenes and ethyl ethers are formed. Draw their structures. Explain which is or are likely to be the main product(s) in each reaction. In case of formation of two isomers of alkenes, explain which is formed in greater proportion CH3 CH3 H3C-C H -Br CH3 EtOHarrow_forwardReaction of 2-methylpropene with CH3OH in the presence of H2SO4 catalyst yieldsmethyl tert-butyl ether, CH3OC(CH3)3, by a mechanism analogous to that of acid- catalyzed alkene hydration. Write the mechanism, using curved arrows for each step.arrow_forwardCompound A (C6H14) forms three different monochlorides by photochemical chlorination. One of these monochlorides is inert to E2 elimination. The other two monochlorides produce the same alkene B (C6H12) when heated with potassium tert-butoxide in tert-butyl alcohol.Identify compound A, the three monochlorides, and alkene B.arrow_forward
- Hydrocarbon A, C8H12 absorbs 3 equiv. of hydrogen to give B, C8H18 when hydrogenated over a Pd/C catalyst. Treatment of A with aqueous H2SO4 and Hg(II) gives a single ketone, C. Oxidation of A with KMnO4 gives CO2 and the two carboxylic acids D & E shown below. What would be a structure for A?arrow_forwardCompound 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 throughoutarrow_forwardNitromethane is reacted with ethyl prop-2-enoate with EtO-Na+, EtOH 3 equivalents to give the product X(C16). X then reacts with H2/Raney Ni to give the product Y(C14), which in turn reacts with Na to give Z (C12). Indicate which products X, Y and Z are.arrow_forward
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