Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 4.SE, Problem 53AP
trans-Decalin is more stable than its cis isomer, but cis-bicyclo[4.1.0]-heptane is more stable than its trans isomer. Explain.
![Chapter 4.SE, Problem 53AP, trans-Decalin is more stable than its cis isomer, but cis-bicyclo[4.1.0]-heptane is more stable than](https://content.bartleby.com/tbms-images/9781305080485/Chapter-4/images/80485-4.se-53ap-question.jpg)
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Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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- invert the stereo chemistry of alkenes from trans to cisarrow_forwardTake a look at the butane conformers below. Identify: (a)Which is an anti conformation in Newman? (b)Which is a Gauche conformation? (c)Which is the more stable Sawhorse conformer? (d)Which has the same potential energy/strain with ALS?arrow_forwardDraw a stereoisomer of cis-1,3-dibromocyclohexane. (Note that the question asks for a different stereoisomer of the named compound and not the патed compound itself) Use the wedge/hash bond tools to indicate stereochemistry where it exists. In cases where there is more than one answer, just draw one.arrow_forward
- 3. Draw the bond line structure that corresponds to the names of the following compounds: a) (S)-6-chloro-1-methylcyclohexa-1,4-diene. b) (S)-hept-5-yn-2-olarrow_forwardGibbs free energy differences between axial-substituted and equatorial-substituted chair conformations of cyclohexane were given in Table 2.4. (a) Calculate the ratio of equatorial to axial tert-butylcyclohexane at 25C. (b) Explain why the conformational equilibria for methyl, ethyl, and isopropyl substituents are comparable but the conformational equilibrium for tert-butylcyclohexane lies considerably farther toward the equatorial conformation.arrow_forwardConsider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forward
- Rank the following alkenes in order of increasing stability: CH,=C(CH3)CH,CH3, CH2=CHCH(CH3)2, and (CH3),C=CHCH3.arrow_forwardHow many isomers (structural, geometric, and stereo) have the formula C5H10, and have "cyclo" in their name? (i.e. they contain a ring) 4 06 07 5arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forward
- 24. Trans-Decalin is more stable than its cis isomer, but cis-bicyclo[4.1.0] heptane is more stable than its trans isomer. Explain. H фф Н H trans-Decalin cis-Bicyclo[4.1.0]heptanearrow_forwardV2arrow_forward3. The heat of hydrogenation for allene, H½C = C= CH2, to yield propane is – 295 kJ/mol, and the heat of hydrogenation for a typical monosubstituted alkene such as propene is -126 kJ/mol. Is allene more stable or less stable than you might expect for a diene ? Explain.arrow_forward
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