Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 10, Problem 7PP
Practice Problem 10.7
Chlorination reactions of certain
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Carbon–carbon bond dissociation enthalpies have been measured for many alkanes. Identify the alkane in each of the following pairs that has the lower carbon–carbon bond-dissociation enthalpy, and explain the reason for your choice. (a) Ethane or propane (b) Propane or 2-methylpropane (c) 2-Methylpropane or 2,2-dimethylpropane (d) Cyclobutane or cyclopentane
Compound X, C,4H12Br2, is optically inactive. On treatment with strong base, X gives hydrocarbon Y, C14H10: Compound Y absorbs 2 equivalents of
hydrogen when reduced over a palladium catalyst to give z (C14H14) and reacts with ozone to give one product, benzoic acid (C,Hg02). Draw the
structure of compound Z.
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• Ignore alkene stereochemistry.
• If more than one structure fits the description, draw them all.
• 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.
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2. (a) The heat of combustion of liquid benzaldehyde (C6H5CHO) is -3393 kJ/mole, and that of
liquid 2,4,6-cycloheptatrien-1-one (C₂H6O) is -3470 kJ/mole. Assume that both
combustions result in products, CO2 and H₂O, that are entirely in the gas phase. Using
the standard chemical equation for the combustion of a hydrocarbon, find the heats of
formation (in kJ/mol) for both benzaldehyde and 2,4,6-cycloheptatrien-1-one in the
liquid phase.
(b) Consider the isomerization from 2,4,6-cycloheptatrien-1-one to benzaldehyde. What is
the enthalpy change (in kJ/mol) for this reaction? Is it endothermic or exothermic?
(c) If ArxnS = -18 J/mol-K for the isomerization reaction, find ArxnG at 350 K (in kJ/mol) and
determine if it is spontaneous in the liquid phase at this temperature. For this
calculation, you may assume that ArxnH and ArxnS are constant between 300 and 350 K.
Chapter 10 Solutions
Organic Chemistry
Ch. 10 - Prob. 1PPCh. 10 - Prob. 2PPCh. 10 - Practice Problem 10.3 How would the molecular ion...Ch. 10 - Prob. 4PPCh. 10 - Prob. 5PPCh. 10 - Prob. 6PPCh. 10 - Practice Problem 10.7 Chlorination reactions of...Ch. 10 - Prob. 8PPCh. 10 - Prob. 9PPCh. 10 - Prob. 10PP
Ch. 10 - Prob. 11PPCh. 10 - Practice Problem 10.12 Benzylic radicals, due to...Ch. 10 - Prob. 13PPCh. 10 - Practice Problem 10.14 Show how the following...Ch. 10 - Prob. 15PPCh. 10 - Prob. 16PPCh. 10 - Prob. 17PPCh. 10 - Prob. 18PCh. 10 - Explain the relative distribution of produces...Ch. 10 - 10.20 Which of the following compounds can be...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - 10.25 List in order of decreasing stability all of...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Starting with the compound or compounds indicated...Ch. 10 - Prob. 30PCh. 10 - 10.31 Synthesize each of the following compounds...Ch. 10 - Synthesize each of die following compounds by...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 36PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 38PCh. 10 - Prob. 39PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - 10.41 Hydrogen peroxide and ferrous sulfate react...Ch. 10 - Prob. 42PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...
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- Explain the hybridisation of electron orbitals in a carbon atom (sp, sp2 and sp3), giving a detailed explanation, supported by suitable examples, of how sigma (s) and pi (p) bonds are formed. 2 Explain why alkenes are much more reactive than alkanes towards chlorine (C12) or bromine (Br2) in the dark at room temperature, and why alkanes do not react with HCI (g) or HBr (g) whereas alkenes do. please provide a diagram as wellarrow_forwardG.170.arrow_forwardFree‑radical halogenation can occur with chlorine and a source of direct UV radiation or sunlight. Chlorination of 2,4‑dimethylpentane via radical halogenation leads to the formation of all three of the products shown. Estimate the relative percentages of each product that will be formed using this means of halogenation. Presume that 1 equivalent of chlorine is used.arrow_forward
- 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Which of the alternative chair conformations of lindane is more stable? Explain.arrow_forward1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Using a planar hexagon representation for the cyclohexane ring, draw a structural formula for lindane.arrow_forward1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans isomerism. At one time, a crude mixture of these isomers was sold as an insecticide. The insecticidal properties of the mixture arise from one isomer, known as lindane, which is cis-1,2,4,5-trans- 3,6-hexachlorocyclohexane. Q.) Draw a structural formula for 1,2,3,4,5,6-hexachlorocyclohexane disregarding, for the moment, the existence of cis,trans isomerism. What is the molecular formula of this compound?arrow_forward
- Compounds X and Y both have the formula C7H₁4. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylhexane. The heat of hydrogenation of X is greater than that of Y. Both X and Y react with HCI to give the same single C7H15Cl compound as the major product. What is the structure of X? • In cases where there is more than one answer, just draw one. 23 ▾ Sn [F ChemDoodleⓇ 146arrow_forwardInterpret the acidity of alcohols on the basis of ground-state polarization and stability of the alcoholate anion(indicate and give symbols for bond polarization)! Compare the relative acidity of ethanol and 2-fluoroethanol!arrow_forwardThe boiling point of methylcyclohexane (C7H14, MW 98.2) is 101°C. The boiling point of perfluoromethylcyclohexane (C7F14, MW 350) is 76°C. Account for the fact that although the molecular weight of perfluoromethylcyclohexane is over three times that of methylcyclohexane, its boiling point is lower than that of methylcyclohexane.arrow_forward
- The compound below is treated with chlorine in the presence of light. CH3 CH3CHCH,CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms.arrow_forwardMeasure the C-C-C and C-C-H bond angles in the energy-minimized model of cyclohexene and compare them with those predicted by VSEPR. Explain any differences.arrow_forwardNew hydrocarbon compounds K, L, M and N have been formed from an organic reactions in Dr. Meredith laboratory. She found that compound K and L with molecular formula (C;H14) are unsaturated hydrocarbons with positional isomerism. Meanwhile, the reaction of hydrocarbon from compound M produces carbon dioxide and water when burns in plentiful oxygen. Another observation showed compound N produces three products X, Y and Z when react with chlorine gas in the presence of UV light. Identify the name of unsaturated hydrocarbon compound K and L and draw their possible condensed and skeletal structures. Suggest the IUPAC nomenclature name for compound M and write the complete chemical reaction of compound M when burns in plentiful oxygen. Show the complete mechanism reaction that occur for the formation of products X, Y and Z from compound N.arrow_forward
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