For each of the following molecules, draw the planar line-angle drawing, using wedges and dashes to show stereochemistry. Then, draw both alternative chair conformations. Circle which chair conformation is favored; if the two chair conformations are equal in energy, circle both.. cis-1,3-diethylcyclohexane cis-1,2-dimethylcyclohexane (1S, 3S)-1-(tert-butyl)-3-methylcyclohexane

For each of the following molecules, draw the planar line-angle drawing, using wedges and dashes to show stereochemistry. Then, draw both alternative chair conformations. Circle which chair conformation is favored; if the two chair conformations are equal in energy, circle both.. cis-1,3-diethylcyclohexane cis-1,2-dimethylcyclohexane (1S, 3S)-1-(tert-butyl)-3-methylcyclohexane

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter2: Alkanes And Cycloalkanes

Section: Chapter Questions

Problem 2.35P: Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest...

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Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energy
Following is a planar hexagon representation of L-fucose, a sugar component of the determinants of the A, B, O blood group typing. For more on this system of blood typing, see Chemical Connections: A, B, AB, and O Blood Group Substances in Chapter 25. (a) Draw the alternative chair conformations of L-fucose. (b) Which of them is more stable? Explain.
Following is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (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?
6. Draw the chair conformation and its ring-interconversion isomer of both cis and trans-1-cyclobutyl-2- methylcyclohexane and rank the four structures for stability (1 = most stable to 4 = least stable; no justifications needed). Don't forget to draw in your cyclohexane ring hydrogens!
There are three diastereomers of 2-bromo-1,3-dimethylcyclohexane. (a) Using the orientation of the chair conformation shown below, draw all three diastereomers of 2-bromo-1,3-dimethyleyclohexane. Follow the numbering given when placing the positions of the two methyl groups and make sure that the bromine leaving group remains in the axial position as shown. 1 2 3 Br Diastereomer 1 Diastereomer 2 Diastereomer 3 (b) Only 2 of these diastereomers undergo an E2 reaction with HO-. Based on the nature of the required transition states for E2 reactions, indicate with an asterisks *, which of the ones you drew in part (a) above undergoes an E2 reaction? (c) The diastereomer that does not undergo an E2 reaction, reacts with HO to form the SN2 product instead. Draw the structure of this SN2 product.
[Referenca cis-2,5-dimethyl-1,3-dioxane The structure of cis-2,5-dimethyl-1,3-dioxane is shown above, without stereochemistry. In the most stable chair conformation, predict the orientation of the two methyl group both equat 1 axial and In the sketchpad, draw the structure of cis-2,5-dimethyl-1,3-dioxane. both axial • Draw your ring as a flat hexagon with wedge/dash bonds to indicate stereochemistry. If a group is achiral, do not use wedged or hashed bonds on it. • In cases where there is more than one answer, just draw one.
f) Make models of cis- and trans-1,3-dimethylcyclohexane. Draw a Newman projection and a clear 3D representation of each chair conformation of each isomer. (This requires a total of eight drawings.) Clearly indicate which is the most stable and which is the least stable conformation (for each cis- and trans-) Clearly indicate which is the more stable and which is the less stable isomer. CH3 pass out
Which of the statements below correctly describes the chair conformations of trans-1,4-dimethylcyclohexane? * The lower energy chair conformation contains two axial methyl groups. The two chair conformations are of equal energy. The higher energy chair conformation contains one axial methyl group and one equatorial methyl group. O The higher energy chair conformation contains two axial methyl groups. The lower energy chair conformation contains one axial methyl group and one equatorial methyl group.
4. Draw a chair conformation of the following molecules. Ring flip your original chair, and circle the more stable conformation. cis-1,2-dimethylcyclohexane trans-1-tert-butyl-3-ethylcyclohexane cis-1,4-diisopropylcyclohexane cis-1-butyl-3-methylcyclohexane
10. One cis, trans isomer of 3,5-dimethylcyclohexanol is drawn below (left). Complete the drawings of the alternative chair conformations of this molecule (right), adding methyl substituents in axial and/or equatorial positions, as appropriate. Circle the more stable conformation. H3C,,, ОН OH -ОН CH3
4. Draw the most stable chair conformation of the following disubstituted cyclohexane. Draw carefully positioned intersecting arcs to denote all sources of steric strain for this conformation. CH3 CH3
1. The structure shown below is a dioxane, and it exists in a chair conformation just like cyclohexane. The specific compound is cis-2-methyl-5-tert-butyl-1,3-dioxane. Draw the two chair conformations of this compound. Surprisingly, the conformer with the tert-butyl group in an axial position is preferred. Circle the preferred conformer. In one sentence or less, explain of this observation. C(CH3)3 CH3