Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
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.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Rank the following groups in order of decreasing priority.
−CH=CH2, −CH3, −C≡CH, −H
Why is this chair conformation the most stable trans-1-chloro-3-flurocyclohexane? Wouldn't the conformation with Cl & F in equatorial positions be the most stable conformation?
Rank the following groups in order of decreasing priority.
−H, −CH3, −Cl, −CH2Cl
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...
Knowledge Booster
Learn more about
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
- Draw the meso form of (1R,4R)-cycloheptane-1,4-diol Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound.arrow_forward(a) How many stereogenic double bonds are in octa-1,3,5-triene? How many stereocenters are there? Draw and name the four stereoisomers of octa-1,3,5-triene.arrow_forwardWhich isomer is more stable, cis-decalin or trans-decalin? Explain.arrow_forward
- Construction a qualitative potential energy for rotation about the C C Bond of 1,2-dibromoethane. Which conformation Would you expect to be more stabel? Label the anti and gauche conformations of 1,2 -dibrimoethanaarrow_forwardGiven that the free energy of the twist-boat conformer of cyclohexane is 5.3 kcal/mol greater than that of the chair conformer, calculate the percentage of twist-boat conformers present in a sample of cyclohexane at 25 °C. Does your answer agree with the statement made in Section 3.13 about the relative number of molecules in these two conformations?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_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_forwarda.) Draw B as a hexagon with wedges and dashed wedges to show the stereochemistry of substituents.b.) Draw a stereoisomer of A as a hexagon using wedges and dashed wedges to show the orientation of substituents.arrow_forwardHow many allylic hydrogens does cyclopentene have?arrow_forward
- Consider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forwardWhy is the percentage of molecules with the substituent in an equatorial position greater for isopropylcyclohexane than for fluorocyclohexane?arrow_forwardBetween the cis and trans configuration of 1-chloro-4-methylcyclohexane, which is the most stable stereoisomer and configuration? To prove your argument, draw a model or use a modeling software to model cis- and trans-1-chloro-4-methylcyclohexane (show all the hydrogens and ensure proper chair conformation) and use arrows to show where steric strain occurs.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
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
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License