ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 4.13, Problem 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.
Rank 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.
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. 4.1 - Prob. 1PCh. 4.1 - Problem 4.2 Which of the following is not another...Ch. 4.1 - Problem 4.3 Draw the five constitutional isomers...Ch. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.2 - Draw the five constitutional isomers that have...Ch. 4.4 - Problem 4.7 Give the IUPAC name for each...Ch. 4.4 - Give the IUPAC name for each compound. a....Ch. 4.4 - Problem 4.9 Give the structure corresponding to...Ch. 4.4 - Prob. 10P
Ch. 4.5 - Give the IUPAC name for each compound.Ch. 4.5 - Give the structure corresponding to each IUPAC...Ch. 4.8 - Arrange the following compounds in order of...Ch. 4.9 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4.9 - Prob. 15PCh. 4.9 - Prob. 16PCh. 4.10 - Problem 4.17 a. Draw the three staggered and...Ch. 4.10 - Problem 4.18 Rank the following conformations in...Ch. 4.10 - Problem 4.19 Consider rotation around the...Ch. 4.10 - Calculate the destabilization present in each...Ch. 4.12 - Problem 4.21 Classify the ring carbons as up or...Ch. 4.12 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4.13 - Draw a second chair conformation for each...Ch. 4.13 - Problem 4.24 Draw both conformations for and...Ch. 4.13 - Problem 4.25 Draw the structure for each compound...Ch. 4.13 - Prob. 26PCh. 4.14 - Prob. 31PCh. 4.14 - Prob. 32PCh. 4.15 - Prob. 33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 42PCh. 4 - 4.46 Considering rotation around the bond...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 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 66PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 74PCh. 4 - Prob. 75PCh. 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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