Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 7.SE, Problem 52AP
trans-Cyclooctene is less stable than cis-cyclooctene by 38.5 kJ/mol, but trans-cyclononene is less stable than cis-cyclononene by only 12.2 kJ/mol. Explain.
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The molar heat of combustion of gaseous cyclopropaneis -2089 kJ/mol; that for gaseous cyclopentane is-3317 kJ/mol. Calculate the heat of combustion per CH2group in the two cases, and account for the difference.
Explain the concept of Cyclohexane Conformations ?
1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product.
a.
Provide a balanced chemical equation to show the reaction between 1,4-pentadiene and sulfuric acid. Do not use molecular formulas in the chemical equation except for sulfuric acid.
b.
What reactant is the limiting reagent in this chemical equation? Show calculations to support your answer.
Chapter 7 Solutions
Organic Chemistry
Ch. 7.2 - Calculate the degree of unsaturation in each of...Ch. 7.2 - Prob. 2PCh. 7.2 - Diazepam, marketed as an antianxiety medication...Ch. 7.3 - Give IUPAC names for the following compounds:Ch. 7.3 - Prob. 5PCh. 7.3 - Prob. 6PCh. 7.3 - Prob. 7PCh. 7.4 - Prob. 8PCh. 7.4 - Prob. 9PCh. 7.4 - Prob. 10P
Ch. 7.5 - Which member in each of the following sets ranks...Ch. 7.5 - Prob. 12PCh. 7.5 - Prob. 13PCh. 7.5 - Prob. 14PCh. 7.6 - Prob. 15PCh. 7.8 - Prob. 16PCh. 7.8 - Prob. 17PCh. 7.9 - Show the structures of the carbocation...Ch. 7.9 - Draw a skeletal structure of the following...Ch. 7.10 - Prob. 20PCh. 7.11 - On treatment with HBr, vinylcyclohexane undergoes...Ch. 7.SE - Prob. 22VCCh. 7.SE - Prob. 23VCCh. 7.SE - The following carbocation is an intermediate in...Ch. 7.SE - Prob. 25VCCh. 7.SE - Predict the major product and show the complete...Ch. 7.SE - Prob. 27MPCh. 7.SE - When 1, 3-butadiene reacts with one mole of HBr,...Ch. 7.SE - When methyl vinyl ether reacts with a strong acid,...Ch. 7.SE - Addition of HCl to 1-isopropylcyclohexene yields a...Ch. 7.SE - Addition of HCl to...Ch. 7.SE - Limonene, a fragrant hydrocarbon found in lemons...Ch. 7.SE - Prob. 33MPCh. 7.SE - Calculate the degree of unsaturation in the...Ch. 7.SE - Prob. 35APCh. 7.SE - Prob. 36APCh. 7.SE - Name the following alkenes:Ch. 7.SE - Draw structures corresponding to the following...Ch. 7.SE - Prob. 39APCh. 7.SE - Prob. 40APCh. 7.SE - Prob. 41APCh. 7.SE - Prob. 42APCh. 7.SE - Prob. 43APCh. 7.SE - Draw and name the 17 alkene isomers, C6H12,...Ch. 7.SE - Prob. 45APCh. 7.SE - Prob. 46APCh. 7.SE - Which of the following E, Z designations are...Ch. 7.SE - Prob. 48APCh. 7.SE - trans-2-Butene is more stable than cis-2-butene by...Ch. 7.SE - Prob. 50APCh. 7.SE - Normally, a trans alkene is more stable than its...Ch. 7.SE - trans-Cyclooctene is less stable than...Ch. 7.SE - Prob. 53APCh. 7.SE - Prob. 54APCh. 7.SE - Use Hammond’s Postulate to determine which...Ch. 7.SE - Prob. 56APCh. 7.SE - Predict the major product in each of the following...Ch. 7.SE - Prob. 58APCh. 7.SE - Prob. 59APCh. 7.SE - Prob. 60APCh. 7.SE - Allene (1,2-propadiene), H2C=C=CH2, has two...Ch. 7.SE - The heat of hydrogenation for allene (Problem...Ch. 7.SE - Retin A, or retinoic acid, is a medication...Ch. 7.SE - Prob. 64APCh. 7.SE - tert-Butyl esters [RC02C(CH3)3] are converted into...Ch. 7.SE - Vinylcyclopropane reacts with HBr to yield a...Ch. 7.SE - Prob. 67APCh. 7.SE - Prob. 68APCh. 7.SE - Prob. 69APCh. 7.SE - Prob. 70APCh. 7.SE - Prob. 71APCh. 7.SE - Reaction of 2, 3-dimethyl-l-butene with HBr leads...
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- 1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product. What is the theoretical yield of 2,4-pentanediol expressed in grams? Show calculations. What is the percentage yield of pure 2,4-pentanediol?arrow_forwardIs isomerization of cis and trans -4-methyl-2-pentene possible at room temperature? Explain whyarrow_forwardAs we learned in Chapter 4, monosubstituted cyclohexanes exist as an equilibrium mixture of two conformations having either an axial or equatorial substituent. When R = CH2CH3, Keq for this process is 23.When R = C(CH3)3, Keq for this process is 4000. a.When R = CH2CH3, which conformation is present in higher concentration? b.Which R shows the higher percentage of equatorial conformation at equilibrium? c. Which R shows the higher percentage of axial conformation at equilibrium? d. For which R is ΔGo more negative? e.How is the size of R related to the amount of axial and equatorial conformations at equilibrium?arrow_forward
- The molar heat of combustion of gaseous cyclopropane is -2089 Kj/mol, that for gaseous cyclopentene is -3317 Kj/mol. Calculate the heat of combustion per CH2 group in the two cases and account for the differencearrow_forwardPyrethrins, such as jasmolin II (shown below), are a group of natural compounds that are synthesized by flowers of the genus Chrysanthemum (known as pyrethrum flowers) to act as insecticides. CH3 CH2=CH-CH. CH-C- -HCS 0-CH, CH,-C H2C- ČH, Which is not a functional group or structural feature in jasmolin II? cycloalkane carboxylic acid ester alkenearrow_forwardThe molar heat of combustion of gaseous cyclopropane is -2089 kJ/mol; that for gaseous cyclopentane is -3317 kJ/mol. Calculate the heat of combustion per CH2 group in the two cases, and account for the difference.arrow_forward
- 8. The heat of combustion (per CH₂) of several cycloalkanes is listed below. Based on the data given, which of these cycloalkanes would be considered most stable? Heat of combustion (kJ/CH₂) -686.5 -664.0 -663.6 -659.0 (A) cyclobutane (C) cyclooctane Cycloalkane cyclobutane cyclopentane cyclooctane cyclopentadecane (B) cyclopentane (D) cyclopentadecanearrow_forwardThere are 17 possible alkene isomers with the formula C6H12. Draw structures of the five isomers in which the longest chain has six carbon atoms, and give the name of each. Are any of these isomers chiral? (There are also eight isomers in which the longest chain has five carbon atoms, and four isomers in which the longest chain has four carbon atoms. How many can you find?)arrow_forwardWhy is a substituted cyclohexane ring more stable with a larger group in the equatorial position?arrow_forward
- Why is a 1, 3 - cis disubstituted cyclohexane more stable than its trans isomer?arrow_forward21.) Calculate the enthalpy of hydrogenation of benzene to cyclohexane from the following reactions A,H (kJ/mol) C6H6 (1) + 15/2 02 (g) → 6 CO2 (g) + 3 H20 (1) C6H12 (1) + 9 02 (g) → 6 CO2 (g) + 6 H20 (1) H2 (g) + ½ 02 (g) → H2O (1) -3268 -3920 -285.83 a.) -205 kJ/mol b.) -1507 kJ/mol c.) -938 kJ/mol d.) -366 kJ/molarrow_forwardDetermine the heat of hydrogenation, in kJ/mol, for the compound shown below. H₂C H H CH3arrow_forward
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