below is shown one of the two chair conformations of (15,3S)-3-ethylcyclohexan-1-ol. a. Next to the given structure, draw the other chair conformation that would result were the given structure to undergo a ring flip. DO NOT ROTATE THE STRUCTURE OR TURN IT UPSIDE DOWN. Be sure all axial and equatorial bonds are drawn accurately in your representation. CH₂CH3 OH ring flip b. Tell whether the structure you drew is more stable, less stable, or equally as stable relative to the given structure (a methyl group is bulkier than a hydroxyl) CIRCLE ONE. more stable equally as stable less stable

below is shown one of the two chair conformations of (15,3S)-3-ethylcyclohexan-1-ol. a. Next to the given structure, draw the other chair conformation that would result were the given structure to undergo a ring flip. DO NOT ROTATE THE STRUCTURE OR TURN IT UPSIDE DOWN. Be sure all axial and equatorial bonds are drawn accurately in your representation. CH₂CH3 OH ring flip b. Tell whether the structure you drew is more stable, less stable, or equally as stable relative to the given structure (a methyl group is bulkier than a hydroxyl) CIRCLE ONE. more stable equally as stable less stable

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

Section2.5: Conformations Of Alkanes And Cycloalkanes

Problem 2.9P: Following is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a)...

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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.
Build a model of methylcyclohexane, and use the model to complete the following Newmanprojections of methylcyclohexane in the chair conformation: a. When the methyl group is in an axial or equatorial (circle one) position, the molecule is inits lowest potential energy conformation. b. Label one Newman projection above anti and the other gauche to describe the relationshipbetween the methyl group and C3 of the ring. c. In general, which is a lower PE conformation, anti or gauche? d. Explain how your answer to b and c provide an explanation for why it is more favorable fora large group to be in an equatorial than an axial position.
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?
Compare the following conformers of 1-fluoropropan-1-ol. Match each conformer to their corresponding relative energy. Recall, the more stable the conformer the lower the energy. OH CH3 'F 2. HOH 2nd Highest Energy H 2nd Lowest Energy H3C 3. H. ОН Lowest Energy H 'F Highest Energy ČH3 4. H3C, OH 'F 1. >
8. Consider 1-bromo-2-methylpropane. Draw a Newman projection of the following (when viewed directlyalong the C1-C2 bond) a. staggered conformation of lowest energyb. eclipsed conformation of highest energy
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
2. For the two compounds below, draw the two possible conformations. Circle the conformation(s) that would be the most stable. Remember, though A values were developed for cyclohexanes, they are a good guide for other types of rings as well! OH ço OEt ll ph
a. Draw the structure of this molecule as a hexagon with dash(es) and/or wedge(s). ha -OH b. Draw the other chair conformation. c. Draw the enantiomer of the molecule in its most stable conformation. он H d. Ignoring differences in conformation, how is this molecule related to the one above? Are they the Same molecule, Enantiomers, or Diastereomers? OH H₂ HH₂ POM (CH₂)2
4. Draw the most and least stable conformations of the following substituted cyclohexanes in the chair format (excluding transient conformations like half chair, twist boat and boat). Br BL Br Br
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
5. Draw the Newman Projection of cis-1,2- dimethylcyclopentane looking down the C1-C2 bond. Assume a planar conformation (i.e. the methyl groups would be eclipsed).
b. Draw a Newman projection of the given compound H viewed from C-2 to C-3 orientated according to the first template. Then use the Newman projection to demonstrate the most stable conformation around the C2-C3 bond according to the second template. (Hint: Order of decreasing group size 'Pr > CH2CH3 > CH3 > OH > Br > H] NH2 Me Ме H 'Pr Given conformation Most stable conformation