Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
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.
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Br₂
CH₂Cl₂
You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
Do not include counter-ions, e.g., Na, I", in your answer.
What is [2 + 2] Cycloadditions ?
(a) Draw all stereoisomers formed by monobromination of the cis and trans isomers of 1,2-dimethylcyclohexane drawn
below. (b) How do the products formed from each reactant compare-identical compounds, stereoisomers, or
constitutional isomers?
cis-1,2-dimethylcyclohexane
trans-(1R.2S)-dimethylcyclohexane
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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- Draw 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_forwardWhich will be more stable, cis or trans-1,4-tert-butylcyclohexane? Explain by drawing their structures?arrow_forwardRank the following alkenes in order of increasing stability: CH,=C(CH3)CH,CH3, CH2=CHCH(CH3)2, and (CH3),C=CHCH3.arrow_forward
- (a) Draw the chair form of cis-1,4-dimethylcyclohexane. Show the strains present, and calculate the total strain energy. CH3 H3C cis-1,4-dimethylcyclohexane (b) Draw the isomer resulting from a ring-flip. Show the strains present, and calculate the total strain energy. (c) Which of the two isomers is most stable? Which is favored in the equilibrium between them? (d) Draw the chair form of the trans-diequatorial isomer. Show and calculate the total strain energy.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-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forward
- Gibbs 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_forwardWhich compound is more stable: cis-1,2-dimethylcyclopropane or trans-1,2- dimethylcyclopropane? Explain your answer.arrow_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_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_forwardDraw a stereoisomer of cis-1,2-dimethylcyclohexane. (Note that the question asks for a different stereoisomer of the named compound and not the named 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. Y TAYY n[] ChemDoodlearrow_forward
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