Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
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 4, Problem 47P
Consider the cis and trans isomers of 1,3-di-tert-butylcyclohexane (build molecular models). What unusual feature accounts for the face that one of these isomers apparently exists in a twist boat conformation rather than a chair conformation?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
What is the most stable conformation for trans-1,2-dichlorocyclohexane. Describe and explain briefly
Write a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.
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 4 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGP
Additional Science Textbook Solutions
Find more solutions based on key concepts
For Practice 1.1
Is each change physical or chemical? Which kind of property (chemical or physical) is demonst...
Principles of Chemistry: A Molecular Approach (3rd Edition)
Rank the given solvents in decreasing order of their ability to dissolve each compound. Solutes
Organic Chemistry (9th Edition)
A stream of pure cyclopentane vapor flowing at a rate of 1550 L/s at 150°C and 1 atm enters a cooler in which 6...
Elementary Principles of Chemical Processes, Binder Ready Version
The folding of protein made up of 200 glycine molecules and 200 aspartic acids must be explained. Concept Intro...
Living by Chemistry
A compound that contains only C and H was burned in excess O2 to give CO2 and H2O. When 0.270 g of the compound...
General Chemistry: Atoms First
Look up the physical properties of several of the compounds you will be making in your lab from several differe...
The Organic Chem Lab Survival Manual: A Student's Guide to Techniques
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
- Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.arrow_forwardFollowing are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used solvent for organic compounds. Piperidine is found in small amounts in black pepper (Piper nigrum). (a) Complete the Lewis structure of each compound by showing all unshared electron pairs. (b) Predict bond angles about each carbon, oxygen, and nitrogen atom. (c) Describe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.arrow_forwardIs there a difference in the stability of the two cyclohexane conformations?arrow_forward
- There are four cis,trans isomers of 2-isopropyl-5-methylcyclohexanol:(a) Using a planar hexagon representation for the cyclohexane ring, draw structural formulas for the four cis,trans isomers.(b) Draw the more stable chair conformation for each of your answers in part (a).(c) Of the four cis,trans isomers, which is most stable? (Hint: If you answered thispart correctly, you picked the isomer found in nature and given the name menthol.)arrow_forward4. possible equatorial axial relationships for the cis and trans for the compound CH2CH3 CH Which is the conformer? Explain (in not more than two lines in your own words)arrow_forwardChemistry 9) Write Newman projections for the gauche and anti-conformations of 1,2- dibromoethane (BrCH2CH2Br). Which conformation is more stable than the other and explain why?arrow_forward
- 2) Which molecule is more stable cis 1,2-dimethylcyclohexane or trans 1,2-dimethylcyclohexane based on their chair conformations?arrow_forwardCyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq.arrow_forwardPerspective drawings of Chair and Boat Conformers fo Cyclohexane (C6H12). Note it is impossible to place all the carbons in the same plane without straining the bonds. Take two opposite carbons and pull both of them up to make one conformation adn then pull one of them down to make the other conformation. Can you inercovert one conformer int othe other without breaking any bonds? Explain why these represent conformers and not isomers.arrow_forward
- what is the most stable conformation of (1R, 2S, 5R)-1,2,5-trimethylcyclohexanearrow_forward4.(a). Draw the structures of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4- Dibromocyclohexane. 4(b). Draw the most stable conformers of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4-Dibromocyclohexane. 4(c)Which is more stable? (i) cis-1,4-Dibromocyclohexane or (ii) trans-1,4- Dibromolcyclohexane. Explain the reason for your choice.arrow_forwardSquare planar molecules with formula AB2C2 and octahedral molecules with formulas AB4C2 and AB3C3 feature diastereoisomers. Recall that trigonal bipyramidal geometry features two distinct positions: axial and equatorial. Draw all diastereoisomers for trigonal bipyramidal molecules with formula (a) AB4C and (b) AB3C2. You must indicate the stereochemistry using full and dashed wedges and label all positions as either axial (ax) and equatorial (eq)..arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher: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