Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 4, Problem 4.24P
Draw both conformations for
which conformation (if any) is more stable.
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Write a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.
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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.
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 4.1PCh. 4 - Problem 4.2 Which of the following is not another...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Problem 4.7 Give the IUPAC name for each...Ch. 4 - Give the IUPAC name for each compound. a....Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.10P
Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound.
a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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- Is there a difference in the stability of the two cyclohexane conformations?arrow_forwardDetermine which cyclohexane structure has the MOST energy (is the LEAST stable)?arrow_forwardPerform a conformational analysis of 1-bromo-2-chloroethane, BrCH2CH2Cl. Pay attention to the relative energies of the various conformations, but do not concern yourself with the actual energy values.arrow_forward
- Draw the four possible positions, the cis and trans positions of the methyl groups for both the chair and boat conformations, of 1,4-dimethylcyclohexane. Label each as cis or trans and identify the highest in energy.arrow_forwardRank the conformations of n-butane with reference to its potential energy from the most stable to the least stable. Rank from the most stable to the least stable.To rank items as equivalent, overlap them.arrow_forwardConsider the isomers of tert-butylcyclohexanol in conformational structures. Two are cis-2-tert-butylcyclohexanol and two are cis-3-tert-butylcyclohexanol. Indicate which is the more stable conformation for each pair, and indicate which of all four conformations is the most stable. FIX a box OH HO OH A Select the more stable conformation of cis-2-tert-butylcyclohexanol. B OD C B C D ☐A C OH Select the more stable conformation of cis-3-tert-butylcyclohexanol.arrow_forward
- What is the most stable conformation for trans-1,2-dichlorocyclohexane. Describe and explain brieflyarrow_forwardWhich is more stable: cis- or trans-1-(1-ethylpropyl)-3-methylcyclohexane? Draw the most stable conformer for each of the molecules.arrow_forwardHow To Draw the Two Conformations for a Substituted Cyclohexane ?arrow_forward
- Draw the formula for all the possible chair conformations of the following cyclohexanes. Indicate the stable conformer.arrow_forwardPlace the methyl groups by drawing the axial and equatorial positions on the cyclohexane structure in the chair conformations next to the cyclohexane derivatives named below.arrow_forwardFor 1,2-dichloroethane: (a) Draw Newman projections for all eclipsed conformations formed by rotation from 0 to 360° about the carbon-carbon single bond. (b) Which eclipsed conformation(s) has the lowest energy? Which has the highest energy? (c) Which, if any, of these eclipsed conformations are related by reflection?arrow_forward
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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