Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 3.15, Problem 54P
a. Calculate the energy difference between the two chair conformers of trans·1,4-dimethylcyclohexane.
b. What is the energy difference between the two chair conformers of cis-1,4-dimethylcyclohexane?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
a. Calculate the energy difference between the two chair conformers of trans-1,4-dimethylcyclohexane. b. What is the energy difference between the two chair conformers of cis-1,4-dimethylcyclohexane?
4. Perform a conformational analysis on cyclohexane derivative I. Draw out both possible conformers and circle
Using A, U, and G values estimate the energy difference (DG)
the preferred (lowest energy) conformer
between the two conformers and predict the approximate ratio of the two conformers at room temperature
Hj C
Br
cyclohexane I
Analyze the two Newman projections and determine the relationship between the two. How would you describe the relation
between conformations when they are maintained at a temperature too low to permit them to interconvert?
CH3
CH3
Br.
H
H
H
H
A. Identify the relationship.
They are identical.
They are structural isomers.
They are stereoisomers.
They are conformers.
H
H
-I
H
Br
H
B. What is the relationship at low temperatures?
They are identical.
They are conformational diastereomers.
They are structural isomers.
They are conformational enantiomers.
Chapter 3 Solutions
Organic Chemistry (8th Edition)
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structure of a compound with molecular...Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Prob. 6PCh. 3.1 - Draw the structure for each of the following: a....Ch. 3.1 - Name the following compounds: a. CH3OCH2CH3 b....Ch. 3.2 - Prob. 9PCh. 3.2 - Draw the structure for each of the following: a....Ch. 3.2 - Give each substituent on the nine-carbon chain a...Ch. 3.2 - Prob. 14P
Ch. 3.3 - What is each compounds systematic name?Ch. 3.3 - Prob. 16PCh. 3.3 - Prob. 17PCh. 3.3 - Prob. 18PCh. 3.3 - Prob. 19PCh. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 21PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Prob. 25PCh. 3.6 - Prob. 26PCh. 3.7 - Prob. 27PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Draw condensed and skeletal structures for each of...Ch. 3.7 - For each of the following, give the systematic...Ch. 3.8 - Predict the approximate size of the following bond...Ch. 3.9 - Prob. 32PCh. 3.9 - Prob. 33PCh. 3.9 - Prob. 34PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.10 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - Prob. 38PCh. 3.10 - Prob. 39PCh. 3.11 - a. Draw all the staggered and eclipsed conformers...Ch. 3.11 - Prob. 41PCh. 3.11 - Using Newman projections, draw the most stable...Ch. 3.12 - The bond angles in a regular polygon with n sides...Ch. 3.12 - Prob. 44PCh. 3.13 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.14 - Using the data in Table 3.9, calculate the...Ch. 3.14 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.15 - Prob. 48PCh. 3.15 - Which has a higher percentage of the...Ch. 3.15 - a. Draw the more stable chair conformer of...Ch. 3.15 - For each of the following disubstituted...Ch. 3.15 - a. Draw Newman projections of the two conformers...Ch. 3.15 - a. Calculate the energy difference between the two...Ch. 3 - a. How many hydrogen does an alkene with 17...Ch. 3 - Draw the structure of octane and isooctaneCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 56PCh. 3 - a. What is each compounds systematic name? b. Draw...Ch. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - Draw a skeletal structure for an alkane that has...Ch. 3 - What is each compounds systematic name? a....Ch. 3 - Which bus a. the higher boiling point:...Ch. 3 - a. Draw Newman projections of the two conformers...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - Prob. 66PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 69PCh. 3 - Draw skeletal structures for the following: a....Ch. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 72PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Draw the two chair conformers for each of the...Ch. 3 - Why are lower molecular weight alcohols more...Ch. 3 - a. Draw a potential energy diagram for rotation...Ch. 3 - For each of the following compound, determine...Ch. 3 - How many ethers have molecular formula C5H12O?...Ch. 3 - Draw the most stable conformer of the following...Ch. 3 - What is each compounds systematic name?Ch. 3 - Calculate the energy difference between the two...Ch. 3 - The most stable from of glucose (blood sugar) is a...Ch. 3 - What is each compound s systematic name?Ch. 3 - Explain the following: a. 1-Hexanol has a higher...Ch. 3 - One of the chair conformers of cis-...Ch. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Name the following compounds:Ch. 3 - Prob. 88PCh. 3 - Using the data obtained in Problem 85, calculate...Ch. 3 - Draw the conformers for the following...
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 energy difference between the two chair conformers of cis-1,4-dimethylcyclohexane?arrow_forwardCyclohexane structures can have two chair conformations. Draw the alternate conformation of the structure shown below. Rotations of the structure are not allowed. Br CI Flip Harrow_forwardCalculate the energy difference between the two chair conformers of trans-1,2-dimethylcyclohexane.arrow_forward
- Which statement is true about these conformers? H. H. H H CH3 H3C H. H,C H,C H. H. A O A and B are equally stable O Difficult to predict O A more stable than B ) B more stable thanarrow_forward6) Draw the energetically favored (more stable) chair conformer of the following cyclohexane. H3C OH 110arrow_forwardH H,C OH C2 C3 HO CH3 H Which of the following is the most stable staggered conformer? H. Me OH Me OH Me. OH Me. OH Me OH но H. Me H H Conformer A Conformer B Conformer C Conformer B because the anti OH groups avoid hydrogen bonding, which is a destabilizing effect. Conformer A because there are only two gauche interactions, and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer C because there is no steric strain for Me-OH gauche interactions and hydrogen bonding between the two OH groups is a stabilizing effect. Conformer B because the large OH groups are anti to each other.arrow_forward
- Construct the chair structures with the molecular models for trans-1-ethyl-3-methylcyclohexane. Find the energy of each conformer, the equilibrium constant Keq, and the percentage of each conformer at 25oC. Indicate which conformer is more stable.arrow_forwardAs we learned in Chapter 4, monosubstituted cyclohexanes exist as an equilibrium mixture of two conformations having either an axial or equatorial substituent. When R = CH2CH3, Keq for this process is 23.When R = C(CH3)3, Keq for this process is 4000. a.When R = CH2CH3, which conformation is present in higher concentration? b.Which R shows the higher percentage of equatorial conformation at equilibrium? c. Which R shows the higher percentage of axial conformation at equilibrium? d. For which R is ΔGo more negative? e.How is the size of R related to the amount of axial and equatorial conformations at equilibrium?arrow_forwardDraw 2 isomenthol chair conformers. Include axial and equatorial groups. Explain which is more stable.arrow_forward
- 1. Name and draw all possible isomers of trimethylcyclopropane. Which of the isomers is chiral?2. If this is chiral, then is it an R or S isomer?arrow_forwardWhich of the following best explains the reason for the relative stabilities of the conformers shown? II. H3C CH3 I. H CH3 ... -H -- H. H3C H A I has more steric strain. B Il has more torsional strain. I has more torsional strain. D II has more steric strain.arrow_forward4. Barriers to Rotation. What is the rotational barrier (that is, the energy difference between the lowest- and highest-energy conformers) for 2,2-dimethylpropane when the molecule is rotated about the C2-C3 bond?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