Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 4.8, Problem 19P
Identify each substituent in the following compound as axial or equatorial, and tell whether the conformation shown is the more stable or less stable chair form (green = Cl):
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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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- cis-1, 2-Dimethylcyclobutane is less stable than its trans isomer, but cis-l, 3-dimethylcyclobutane is more stable than its trans isomer. Draw the most stable conformations of both, and explain.arrow_forwardDraw a chair conformation of 1,4-dimethylcyclohexane in which one methyl group is equatorial and the other is axial. Draw the alternative chair conformation and calculate the ratio of the two conformations at 25C.arrow_forwardmyo-Inositol, one of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-inositol.arrow_forward
- Conformer E is a (cis/trans) isomer. A conformational ring flip of conformer E will yield conformer F in which the substituent on carbon 1 will be (axial/equatorial/neither) and the substituent on carbon 3 will be (axial/equatorial/neither). Conformer (E/F) will be more stable.arrow_forwardDraw Newman's projections along the C3¬C4 bond to show the most stable and least stable conformations of 3-ethyl-2,4,4-trimethylheptane.arrow_forwardConsider rotation around the C2–C3 single bond of 2-methylpentane. Using the Newman projection templates shown below, (i) draw all possible conformations (ii) arrange these four conformations in the order most stable to least stablearrow_forward
- Consider the substituted cyclohexane shown in the ball-and-stick model.a.Label the substituents on C1, C2, and C4 as axial or equatorial. b. Are the substituents on C1 and C2 cis or trans to each other? c.Are the substituents on C2 and C4 cis or trans to each other? d.Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forwardConsider the substituted cyclohexane shown in the ball-and-stick model.a. Label the substituents on C1, C2, and C4 as axial or equatorial.b. Are the substituents on C1 and C2 cis or trans to each other?c. Are the substituents on C2 and C4 cis or trans to each other?d. Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forward1) Draw the molecule to which the Newman plot below belongs. 2) a) Draw the Newman projection of the most unstable and stable conformations based on the C2-C3 carbons of butane. b) Draw the most stable conformation of cis-1-methyl-3-ethylcyclohexane. 3) Which of the following molecules are structural isomers with each other?arrow_forward
- A1. Draw the most stable conformations for: a)1-methyl-1-propylcyclohexane b)Trans-1-methyl-2-propylcyclohexane c)Cis-1-methyl-2-propylcyclohexanearrow_forwardDraw the most stable conformation of trans-1-tert-butyl-4 chlorocyclohexane.arrow_forwardDraw a Newman projection of the most and the least stable conformation of the following compounds (sighting along the C2-C3 bond): a) 2,3-dimethylbutane b) 1,4-dichlorobutane c) pentane (assign strain energy to each conformation) Please explain how you got your answers.arrow_forward
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