Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter FRP, Problem 21P
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5. Compound A, C 10H 18O, undergoes reaction with dilute H 2SO 4 at 50 °C to yield a mixture of two alkenes, C 10H 16. The major alkene B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Which of the following reactions are correct.
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?
Hydrocarbon X has the formula C6H12.X reacts with one molar equivalent of hydrogen in the presence of a palladium catalyst to form a product having 12 primary hydrogens.Treatment of X with ozone followed by zinc in aqueous acid gives a mixture two aldehydes.What is the structure of X?
Chapter FRP Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
Ch. FRP - Prob. 1PCh. FRP - 2. Which member of these pairs is the more polar?...Ch. FRP - Prob. 3PCh. FRP - Describe how solubility could be used to...Ch. FRP - 5. Though they each contain only one type of...Ch. FRP - Predict the products from each of the following...Ch. FRP - Prob. 7PCh. FRP - Prob. 8PCh. FRP - Prob. 9PCh. FRP - Prob. 10P
Ch. FRP - Predict the products from each of the following...Ch. FRP - Prob. 12PCh. FRP - 13. Starting with propyne and using any other...Ch. FRP - Bromination of 2-methylbutane yields predominantly...Ch. FRP - Prob. 15PCh. FRP - Account for the following observations with...Ch. FRP - Prob. 17PCh. FRP - Prob. 18PCh. FRP - Heating 1, 1,1-triphenylmethanol with ethanol...Ch. FRP - (a) Which of the following halides would you...Ch. FRP - An alkane (A) with the formula C6H14 reacts with...Ch. FRP - Prob. 22PCh. FRP - Prob. 23PCh. FRP - Dehydrohalogenation of meso-1, 2-dibromo-1,...Ch. FRP - Prob. 25PCh. FRP - Prob. 26PCh. FRP - 27. (R)-3-Methyl-1-pentene is treated separately...Ch. FRP - Prob. 28PCh. FRP - Prob. 29PCh. FRP - Prob. 30PCh. FRP - Prob. 31PCh. 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. 35PCh. FRP - 36. Compound X shows a strong IR absorption band...Ch. FRP - Prob. 37PCh. FRP - 38. In addition to more highly fluorinated...Ch. FRP - Fluorination of (R)-2-flurobutane yields a mixture...Ch. FRP - Prob. 40PCh. FRP - Prob. 41P
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- 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.arrow_forwardDetermine a possible structure for an alkene, X, formula C9H14, on the basis of the following information: X adds one mole of hydrogen on catalytic hydrogenation. On treatment with hot basic KMnO4 followed by acidification, X yields the following dicarboxylic acid.arrow_forward2-Methylpropene reacts with cold aqueous sulfuric acid to give A(C4H10O). Treatment of A with sodium metal in anhydrous THF followed by methyl iodide gives B(C5H12O).Draw the structure of B.arrow_forward
- 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.arrow_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 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_forwardA compound with formula C7H12O is treated with sodium borohydride in methanol to yield 2,2-dimethylcylopentanol. Write a reaction scheme showing the structures of the reactant, the reagents, and the product. Will the product be optically active? Explain.arrow_forward
- Compounds 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_forward2 methylbutene react with Hbr to givearrow_forward5B 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_forward
- 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.arrow_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_forwardDraw a structural formula for the alkene with the molecular formula C5H10 that reacts with Br2 to give each product.arrow_forward
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