EP ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582453
Author: Brown
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 2.5, Problem 2.9P
Following is a chair conformation of cyclohexane with the carbon
- (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4.
- (b) Which of these hydrogens are equatorial? Which are axial?
- (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Consider 1-bromopropane, CH3CH2CH2Br.
(a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°).
(b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°).
(c) Which of these is the lowest energy conformation?
(d) Which of these conformations, if any, are related by reflection?
4. (a) Draw a skeletal (line-bond) structure for 3,4-dimethylhexane.
(b) Draw a sawhorse representation of any staggered conformation of this molecule looking down the
carbon-3 to carbon-4 bond.
(c) Draw a Newman projection looking down the carbon-3 to carbon-4 bond of the same conformation
that you drew as a sawhorse representation.
Draw the alternative chair conformations for the cis and
trans isomers of 1,2-dimethylcyclohexane, 1,3-
dimethylcyclohexane, and 1,4-dimethylcyclohexane. (a
) Indicate by a label whether each methyl group is axial
or equatorial. (b) For which isomer(s) are the alternative
chair conformations of equal stability? (c) For which
isomer(s) is one chair conformation more stable than
the other?
Chapter 2 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
Ch. 2.2 - Do the line-angle formulas in each pair represent...Ch. 2.2 - Draw line-angle formulas for the three...Ch. 2.3 - Write IUPAC names for these alkanes.Ch. 2.4 - Combine the proper prefix, infix, and suffix and...Ch. 2.4 - Write the molecular formula, IUPAC name, and...Ch. 2.4 - Write molecular formulas for each bicycloalkane,...Ch. 2.4 - Prob. 2.7PCh. 2.5 - For 1,2-dichloroethane: (a) Draw Newman...Ch. 2.5 - Following is a chair conformation of cyclohexane...Ch. 2.5 - Draw the alternative chair conformation for the...
Ch. 2.5 - Draw a chair conformation of...Ch. 2.6 - Which cycloalkanes show cis, trans isomerism? For...Ch. 2.6 - Following is a planar hexagon representation for...Ch. 2.6 - Here is one cis,trans isomer of...Ch. 2.6 - Prob. AQCh. 2.6 - Prob. BQCh. 2.6 - Prob. CQCh. 2.7 - Arrange the alkanes in each set in order of...Ch. 2 - Write a line-angle formula for each condensed...Ch. 2 - Write the molecular formula of each alkane.Ch. 2 - Using parentheses and subscripts, provide an even...Ch. 2 - Which statements are true about constitutional...Ch. 2 - Prob. 2.20PCh. 2 - Each member of the following set of compounds is...Ch. 2 - Each of the following compounds is an amine...Ch. 2 - Each of the following compounds is either an...Ch. 2 - Draw structural formulas and write IUPAC names for...Ch. 2 - Draw structural formulas for all of the following....Ch. 2 - Write IUPAC names for these alkanes and...Ch. 2 - Write structural formulas and line-angle formulas...Ch. 2 - Explain why each is an incorrect IUPAC name and...Ch. 2 - For each IUPAC name, draw the corresponding...Ch. 2 - Write the IUPAC name for each compound.Ch. 2 - Prob. 2.31PCh. 2 - Torsional strain resulting from eclipsed CH bonds...Ch. 2 - How many different staggered conformations are...Ch. 2 - Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a...Ch. 2 - Consider 1-bromo-2-methylpropane and draw the...Ch. 2 - trans-1,4-Di-tert-butylcyclohexane exists in a...Ch. 2 - From studies of the dipole moment of...Ch. 2 - Prob. 2.38PCh. 2 - Following are the alternative chair conformations...Ch. 2 - Prob. 2.40PCh. 2 - Prob. 2.41PCh. 2 - Draw line-angle formulas for the cis and trans...Ch. 2 - Name and draw structural formulas for all...Ch. 2 - Using a planar pentagon representation for the...Ch. 2 - Gibbs free energy differences between...Ch. 2 - Prob. 2.46PCh. 2 - Calculate the difference in Gibbs free energy in...Ch. 2 - Draw the alternative chair conformations for the...Ch. 2 - Use your answers from Problem 2.48 to complete the...Ch. 2 - There are four cis,trans isomers of...Ch. 2 - Draw alternative chair conformations for each...Ch. 2 - 1,2,3,4,5,6-Hexachlorocyclohexane shows cis,trans...Ch. 2 - Prob. 2.53PCh. 2 - What generalization can you make about the...Ch. 2 - What unbranched alkane has about the same boiling...Ch. 2 - Complete and balance the following combustion...Ch. 2 - Following are heats of combustion per mole for...Ch. 2 - Following are structural formulas and heats of...Ch. 2 - Without consulting tables, arrange these compounds...Ch. 2 - Which would you predict to have the larger (more...Ch. 2 - Following are structural formulas for 1,4-dioxane...Ch. 2 - Following is a planar hexagon representation of...Ch. 2 - On the left is a stereorepresentation of glucose...Ch. 2 - Prob. 2.64PCh. 2 - Prob. 2.65P
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
- Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.arrow_forwardFollowing 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_forwardConsider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forward
- Consider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This group is called an ethyl group and can be considered a sphere about twice the sizeof a methyl group. Draw the following Newman projections sighting down the C1C2 bond... a. The lowest potential energy conformation. b. The highest potential energy staggered conformation.arrow_forwardA trisubstituted cyclohexane with three substituents-red, green, and blue-undergoes a ring-flip to its alternate chair conformation. Identify each substituent as axial or equatorial, and show the positions occupied by the three substituents in the ring-flipped form.arrow_forward(a) Draw the most stable chair conformers of trans-1,3-diisopropylcyclohexane and trans-1,4-diisopropylcyclohexane. (b) Which is more stable: trans-1,3-diisopropylcyclohexane or trans-1,4-diisopropylcyclohexane?arrow_forward
- Draw the most stable conformation of cis-1-tert-butyl-3-ethylcyclohexane. (a) (b) trans-1-tert-butyl-2-methylcyclohexane. (c) trans-1-tert-butyl-3-(1,1-dimethylpropyl)cyclohexane.arrow_forward3)) Draw the most stable chair conformation of a 1,2,4-trimethylcyclohexane (Show all the hydrogens and indicate if the bond is axial or equatorial at the substitution).arrow_forwardH C-Ć- C -CI Following is the structural formula of 1,2– dichloroethane. H H a) Draw Newman projections for all staggered and eclipsed conformations formed by rotation from 0° to 360° about the carbon- carbon single bond. b) Which staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy which has the highest energy?arrow_forward
- Sight along the C2-C1 bond of 2-methylpropane (isobutane).(a) Draw a Newman projection of the most stable conformation.(b) Draw a Newman projection of the least stable conformation.(c) Make a graph of energy versus angle of rotation around the C2-C1 bond.(d) Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 4.0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forwardPertanyaan yang ada pada gambararrow_forwardDraw each compound in its most stable conformation(s). Then draw it in its most symmetric conformation, and determine whether it is chiral.(a) 2-methylbutanearrow_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 LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
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