I arther: Chair conformers Monosubstituted rings The A-value for methyl, ethyl, isopropyl, and t-butyl substitution on a cyclohexane ring are 7.1kJ/mol, 7.3 kJ/mol, 9.0kJ/mol, and 18.8 kJ/mol, respectively.. Me Me 1. Et 95:5 95:5 Bu Bu 97:3 9995:5 Build the molecules and use your model to explain why the increased size of the substituent doe- not have a dramatic effect until you reach t-butyl. In other words, is it possible for the first three substituents (methyl, ethyl, and isopropyl) to achieve conformation in which 1,3-diaxial interactions are minimized? has -value: 0 9kJ/mol. Build the molecule in order to deterr

I arther: Chair conformers Monosubstituted rings The A-value for methyl, ethyl, isopropyl, and t-butyl substitution on a cyclohexane ring are 7.1kJ/mol, 7.3 kJ/mol, 9.0kJ/mol, and 18.8 kJ/mol, respectively.. Me Me 1. Et 95:5 95:5 Bu Bu 97:3 9995:5 Build the molecules and use your model to explain why the increased size of the substituent doe- not have a dramatic effect until you reach t-butyl. In other words, is it possible for the first three substituents (methyl, ethyl, and isopropyl) to achieve conformation in which 1,3-diaxial interactions are minimized? has -value: 0 9kJ/mol. Build the molecule in order to deterr

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry

Section4.SE: Something Extra

Problem 24VC: A trisubstituted cyclohexane with three substituents-red, green, and blue-undergoes a ring-flip to...

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a model of cyclohexane in a chair conformation, and explain why the names “axial” and“equatorial’ are appropriate.
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.
A 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.
The diaxial conformation of cis- 1,3-dimethylcyclohexane is approximately 23kl/mol (5.4 kcal/mol) less stable than the diequatorial conformation. Draw thetwo possible chair conformations, and suggest a reason for the large energydifference.
Draw the highest and lowest energy conformations. In cases where two or three conformations are degenerate, choose only one as your anwser. Use Pr, Me, H, Et in the structures.
Compounds E and F are two isomers of 2,3-dibromopentane drawn in staggered conformations. Which compounds (A–D) in Figure 5.8 are identical to E and F?
Why is this chair conformation the most stable trans-1-chloro-3-flurocyclohexane? Wouldn't the conformation with Cl & F in equatorial positions be the most stable conformation?
.....Draw the Newman pr0jecti0ns 0f the three p0ssible staggered c0nf0rmati0ns 0f2,3-dimethylbutane, viewed thr0ugh the C2—C3 b0nd. What are the relativeenergies of each c0nf0rmati0n?
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Use your answers from Problem 2.48 to complete the table showing correlations between cis,trans and axial,equatorial for disubstituted derivatives of cyclohexane. Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3-dimethylcyclohexane, 1,4-dimethylcyclohexane. (a) Indicate by a label whether each methyl group is axial or equatorial.
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Two conformations of cis-l, 3-dimethylcyclobutane are shown. What is the difference between them, and which do you think is likely to be more stable?