Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 7.SE, Problem 51AP
Normally, a trans
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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.
Do you predict the product to be the cis isomer, the trans isomer, or a mixture of cis and trans isomers? Explain.
The energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).
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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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- As 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_forwardWhich of the following is a cylcloalkane? A or Barrow_forward"Trans alkenes are more stable than cis alkenes because they have fewer steric interactions" What this statement says ?arrow_forward
- Pyrethrins, 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 cyclopentene is -3317 Kj/mol. Calculate the heat of combustion per CH2 group in the two cases and account for the differencearrow_forwardAmong alkenes, alkynes, and aromatic hydrocarbons, onlyalkenes exhibit cis-transisomerism. Why don’t the others?arrow_forward
- The respective Heats of Hydrogenation for three unkown alkenes are determined to be: 118.7 kJ/mol 124.5 kJ/mol 128.0 kJ/mol We have 3 possible structures for these alkenes, as shown. Given the structures shown, which of the following statements is most likely true? Compound A Compound B Compound C The Heat of Hydrogenation for Compound B is 118.7 k/mol, (AND) The Heat of Hydrogenation for Compound A is 128.0 kJ/mol The Heat of Hydrogenation for Compound A is 118.7 kJ/mol (AND) The Heat of Hydrogenation for Compound C is 128.0 kJ/mol O The Heat of Hydrogenation for Compound C is 118.7 kJ/mol O The Heat of Hydrogenation for Compound B is 118.7 k/mol O The Heat of Hydrogenation for Compound A is 118.7 kJ/molarrow_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_forwardDraw the condensed structures and give the systematic names for all the alkenes with molecular formula C6H12, ignoring stereoisomers. (Hint: There are 13.) b. Which of the alkenes have E and Z isomers? c. Which of the alkenes is the most stable? d. Which of the alkenes is the least stable?arrow_forward
- Define trans-Cyclooctene ?arrow_forward1. a. Draw and name the five cycloalkane structures of formula C5H10. Can any of these structures give rise to geometric (cis-trans) isomerism? If so, show the cis and trans stereoisomers. b. Draw and name the eight cycloalkane structures of formula C6H12 that do not show geometric isomerism. c. Draw and name the four cycloalkanes of formula C6H12 that do have cis-trans isomers. 2. Each of the following descriptions applies to more than one alkane. In each case, draw and name two structures that match the description. (a) an isopropylheptane (b) a diethyldecane (c) a cis-diethylcyclohexane (d) a trans-dihalocyclopentane (e) a (2,3-dimethylpentyl)cycloalkane (f) a bicyclononane 3. 2. refer to the photo attached and answer the ff.3-33, 3-34arrow_forward1. Although there is only one alkene with the formula C2H4 (ethene) and only one with the formula C3H6 (propene), there are several alkenes with the formula C4H8. Draw all of the possible bond line structures for alkenes with the formula C4H3 including all possible structural and stereoisomers.arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
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