Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 5, Problem 51P
(Use models co solve this problem.) Write conformational structures for all of the stereoisomers of 1,3-diethylcyclohexane. Label pairs of enantiomers and meso compounds if they exist.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
3)- Determine the total number of conformers and draw the Chair Structures of the conformers for the Tri-substituted
cyclohexane structure given below (i.e., "A"). Draw the relative energy diagram for the possible conformers for the
cyclohexane structure below. Note, draw only the required structures for the conformers of A. Also, include
hydrogen atoms wherever there are substituents on all of your chair conformers.
Answer (Total #of Conformers):
Chair Structures:
Relative Energy Diagram
8 bas roll
3
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).
It is easy to imagine a cyclohexane as a flat hexagon and a lot of the time we draw it
that way. Looking at 1,3,5-triethylcyclohexane we cannot tell the stability of the
molecule from looking at the flat 2D drawing. Explain why we need to look at the 3D
configuration and what conformation (axial,equatorial) would each of the three ethyl
groups be in for the most stable configuration.
Chapter 5 Solutions
Organic Chemistry
Ch. 5 - Prob. 1PPCh. 5 - Prob. 2PPCh. 5 - Prob. 3PPCh. 5 - Prob. 4PPCh. 5 - Prob. 5PPCh. 5 - Prob. 6PPCh. 5 - Prob. 7PPCh. 5 - Practice Problem 5.8 Write three-dimensional...Ch. 5 - Prob. 9PPCh. 5 - Prob. 10PP
Ch. 5 - Practice Problem 5.11 List the substituents in...Ch. 5 - Prob. 12PPCh. 5 - Practice Problem 5.13 Tell whether the two...Ch. 5 - Prob. 14PPCh. 5 - Prob. 15PPCh. 5 - Prob. 16PPCh. 5 - Prob. 17PPCh. 5 - Prob. 18PPCh. 5 - Prob. 19PPCh. 5 - Prob. 20PPCh. 5 - Practice Problem 5.21 The following are formulas...Ch. 5 - Practice Problem 5.22 Write three-dimensional...Ch. 5 - Prob. 23PPCh. 5 - Practice Problem 5.24 Give names chat include (R)...Ch. 5 - Prob. 25PPCh. 5 - Prob. 26PPCh. 5 - Prob. 27PPCh. 5 - Prob. 28PPCh. 5 - Practice Problem 5.29 Write formulas for all of...Ch. 5 - Prob. 30PPCh. 5 - Prob. 31PPCh. 5 - Prob. 32PPCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - 5.35 Designate the (R) or (S) configuration at...Ch. 5 - Prob. 36PCh. 5 - (a) Write the structure of...Ch. 5 - Shown below are Newman projection formulas for...Ch. 5 - 5.39 Write appropriate structural formulas...Ch. 5 - Discuss whether each of the following compounds...Ch. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Compound F has the molecular formula C5H8 and is...Ch. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - For the following molecule, draw its enantiomer as...Ch. 5 - 5.49 (Use models to solve this...Ch. 5 - 5.50 (Use models to solve this...Ch. 5 - (Use models co solve this problem.) Write...Ch. 5 - 5.52 Tartaric acid was an important compound in...Ch. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 1LGPCh. 5 - Prob. 2LGPCh. 5 - Prob. 3LGP
Additional Science Textbook Solutions
Find more solutions based on key concepts
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
Determine [OH], [H+], and the pH of each of the following solutions. a. 1.0 M KCl b. 1.0 M KC2H3O2
Chemistry
The reaction of tert-butyl chloride with methanol (CH3)3CCl + CH3OH (CH3)3COCH3 + HCl tert butyl chloride met...
Organic Chemistry (9th Edition)
1. What did each of the following scientists contribute to our knowledge of the atom?
a. William Crookes
b. E...
Chemistry For Changing Times (14th Edition)
The chemical equation for the reaction of solid aluminum and sulphur to produce aluminium sulphide needs to be ...
Chemistry: Matter and Change
A source of electromagnetic radiation produces infrared light. Which of the following could be the wavelength ...
Chemistry: The Central Science (14th Edition)
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
- What is the most stable conformation for trans-1,2-dichlorocyclohexane. Describe and explain brieflyarrow_forward[Review Topics] [References] Calculate Strain energy for the conformer pictured below, using strain energy increments from the table. Strain Energy for Alkanes Interaction / Compound kJ/mol H: H eclipsing H: CH3 eclipsing CH3 CH3 eclipsing gauche butane cyclopropane cyclobutane cyclopentane cycloheptane cyclooctane H₂ H (Calculate your answer to the nearest 0.1 energy unit, and be sure to specify units, kJ/mol or kcal/mol. The answer is case sensitive.) CH3 CH3 H 4.0 5.8 11.0 3.8 115 110 26.0 26.2 40.5 H kcal/mol 1.0 1.4 2.6 0.9 27.5 26.3 6.2 6.3 9.7 Previous Nextarrow_forward[Review Topics] [References) Calculate strain energy for the conformer pictured below, using strain energy increments from the table. Strain Energy for Alkanes Interaction / Compound kJ/mol kcal/mol H: H eclipsing 4.0 1.0 H: CH3 eclipsing 5.8 1.4 CH3 : CH3 eclipsing 11.0 2.6 gauche butane 3.8 0.9 cyclopropane 115 27.5 cyclobutane 110 26.3 cyclopentane 26.0 6.2 cycloheptane 26.2 6.3 cyclooctane 40.5 9.7 (Calculate your answer to the nearest 0.1 energy unit, and be sure to specify units, kJ/mol or kcal/mol. The answer is case sensitive.) CH, CH CH3 Next Previous H3C Save and E: 15 tv MacBook Air 80 DII DD F4 F5 F6 F7 F8 F9 F10 F11 F12 $ & ) + 4. 5 7 8. %3D Y [ 11 F J + || < coarrow_forward
- I don't understand why the first one and second one are cis and trans respectively. Wouldn't the first one be trans-1,2-dimethylcyclobutane because the torsional strain wouldn't allow the carbons to be in the same conformation. Meaning one of the carbons would be up and then the next would be down and so on. Since both methyl groups are equatorial and the first and second carbons are arranged up and down, wouldn't it be trans. Same logic for the second molecule. Carbon 1, which is attached to the methyl is down, carbon 3 which is attached to the methyl should be down also because of torsional strain, and since both methyl are in axial (or equatorial?), it would be cis. Or is it based off of the way the carbons are positioned in the picture?arrow_forwardQuestion 13 The most stable conformation of line structure X is но ÕH ****** Bu Et H Bu H. Bu Me H 'Bu! Bu HO H OH 'Bu H Et FOH HO OH Ét Me H HO H ÓH I HPOH Ét H OH ÓH Et Me VI II IV V O IV O V None of the given optionsarrow_forwardHello, I was reading an answer from the book Organic Chemistry by Brown et al. The question is 2.51 "Draw alternative chair conformations for each substituted cyclohexane and state which chair is more stable." There are then 4 cyclohexanes (labeled a-d). For the "a" cyclohexane, the substituents are arranged as a combination of axial and equatorial in both chair conformations. However, for the "b," "c," and "d," cyclohexanes one chair has only equatorial substituents, and the other chair has only axial substituents. Why is the "a" chair conformation different? https://www.bartleby.com/solution-answer/chapter-2-problem-251p-organic-chemistry-8th-edition/9781305580350/draw-alternative-chair-conformations-for-each-substituted-cyclohexane-and-state-which-chair-is-more/4532cd91-c341-11e9-8385-02ee952b546earrow_forward
- Draw Newman projections for the anti, eclipsed, gauche and fully eclipsed conformations of Butane. Indicate their relative stabilities and the reasons for your ranking-need to discuss the stresses involved in each case. Using suitable specific conformers of specific structures as examples, explain the difference between (a) angle strain (b) torsional strain and (c) steric strain. Need to draw the confomers and structures 4) Draw the most stable conformers using chair structures of the following: (c) cis-1,2-Dibromocyclohexane (d) trans-1,2-Dibromocyclohexane (e) cis-Decalin (f) trans-Decalin . Draw the most stable conformers of trans-1-Bromo-4-methylcyclohexane and cis-1-Bromo-4-methylcyclohexane. Which is more stable? Explain the reason for your answer. Need to include a discussion of 1,3-Diaxial interactionarrow_forwardHow do you account for the difference in energies between the two staggered conformations of 1,2-dichloroethane? How about for the two eclipsed conformations? Draw all four conformations and, on your drawing, indicate sources of strain – torsional, steric (gauche), steric eclipsed.arrow_forward1: Draw the chain conformer of... 1a. Cyclohexane, label all the axial and equatorial hydrogens 1b. The most stable conformer of ethylcyclohexane 1c. The most sable conformer of trans-1-tert-butyl-3-methylcyclohexanearrow_forward
- 1. The structure shown below is a dioxane, and it exists in a chair conformation just like cyclohexane. The specific compound is cis-2-methyl-5-tert-butyl-1,3-dioxane. Draw the two chair conformations of this compound. Surprisingly, the conformer with the tert-butyl group in an axial position is preferred. Circle the preferred conformer. In one sentence or less, explain of this observation. C(CH3)3 CH3arrow_forwardUsing a planar pentagon representation for the cyclopentane ring, draw structural formula for trans-1,2-dimethylcyclopentane. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • In cases where there is more than one answer, just draw one. • Do not include lone pairs in your answer. They will not be considered in the grading. opy aste C. O O O- [* ChemDoodle I...arrow_forwardDiscuss and compare two possible chair conformations of cis-1,3-dibromocyclohexane compound. Which conformation is more stable? Why? Explain the reason clearly.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
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