Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 3.14, Problem 51P
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
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.
Cyclohexane structures can have two chair
conformations.
Draw the alternate conformation of the structure shown below.
Rotations of the structure are not allowed.
H3C
CF3
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 than
Chapter 3 Solutions
Organic Chemistry
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. 11PCh. 3.2 - Prob. 12PCh. 3.3 - Prob. 13PCh. 3.3 - Prob. 14P
Ch. 3.3 - Prob. 15PCh. 3.3 - Prob. 16PCh. 3.3 - What is each compounds systematic name?Ch. 3.4 - Give two names for each of the following alkyl...Ch. 3.4 - Prob. 19PCh. 3.5 - a. What is each ethers systematic name? 1....Ch. 3.6 - Draw the structures of a homologous series of...Ch. 3.6 - Give each of the following a systematic name and...Ch. 3.6 - Prob. 23PCh. 3.6 - Prob. 24PCh. 3.7 - Are the following compounds primary, secondary, or...Ch. 3.7 - Prob. 26PCh. 3.7 - Prob. 27PCh. 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. 30PCh. 3.9 - Prob. 31PCh. 3.9 - Prob. 32PCh. 3.9 - Rank the following compounds from highest boiling...Ch. 3.9 - Rank the compounds in each set from highest...Ch. 3.9 - Prob. 35PCh. 3.9 - In which solvent would cyclohexane have the lowest...Ch. 3.10 - a. Draw all the staggered and eclipsed conformers...Ch. 3.10 - Prob. 38PCh. 3.10 - Using Newman projections, draw the most stable...Ch. 3.11 - The bond angles in a regular polygon with n sides...Ch. 3.11 - Prob. 41PCh. 3.11 - Prob. 42PCh. 3.12 - Draw 1,2,3,4,5,6-hexachlorocydohexane with a. all...Ch. 3.13 - The chair conformer of fluorocyclohexane is 0.25...Ch. 3.13 - Using the data in Table 3.9, calculate the...Ch. 3.14 - Prob. 46PCh. 3.14 - Which has a higher percentage of the...Ch. 3.14 - For each of the following disubstituted...Ch. 3.14 - 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. 53PCh. 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. 63PCh. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 66PCh. 3 - Prob. 67PCh. 3 - For rotation about the C-3C-4 bond of...Ch. 3 - Prob. 69PCh. 3 - What is each compounds systematic name? a. b. c....Ch. 3 - Prob. 71PCh. 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 - Prob. 80PCh. 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. 85PCh. 3 - Using the data obtained in Problem 85, calculate...
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
- 6) Draw the energetically favored (more stable) chair conformer of the following cyclohexane. H3C OH 110arrow_forwardConstruct 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_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
- Which molecule is a conformer of this one? CH,CH3 H3C но CH3 Select one: CH3 H3C. a. H3CH2C он CH3 Н. Ob. H3CH2C он CH3 CH3 с. но "CH2CH3arrow_forwarda) Draw the two ring flipped conformers of each molecule A and B. Indicate the more stable conformer, respectively. CH3 fCH3 H,C. CH3 H3C. CH3 CI CI A B a) Which is more stable between A and B? Why?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_forward
- Consider 1,2-dimethylcyclohexane.Q: Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?arrow_forwardFor each of the following pairs, give the relationship between the two compounds. You many ignore conformational isomerism here, and any conformers may be considered to be identical compounds.arrow_forwardWrite a structure ( Chair conformation )arrow_forward
- Starting from the wedge-and-dash structure below, rotate the back carbon to provide the Newman projection in the most stable conformation. H₂C H (H3C) 3C H H CH3 →arrow_forwardChoose the statement that is incorrect about rings. اختر احدى الاجابات А. Planar cyclobutane is its most stable conformation. В. Planar cyclopentane would have small angle strain but severe torsional strain. C. The chair conformation of cyclohexane has no angle or torsional strain. D. Cyclopropane has the greatest angle strain. Е. The chair conformation has less torsional strain and fewer nonbonded interactions than the twist boat conformation.arrow_forward1 F1 Q @ 2 F2 W Draw the two chair cyclohexane conformations for the compound shown below. How many substituents are axial in the less stable conformation? >> F10 #3 3 C/ "CI 00 01 02 03 A Moving to another question will save this response. 80 F3 F4 ㅎ... E S4 $ R % 5 F5 T MacBook Air F6 6 Y & 7 F7 U * 00 8 DII F8 ( 9 F9 ) 0 1 I Parrow_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