Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 2.5, Problem 2.11P
Draw a chair conformation of 1,4-dimethylcyclohexane in which one methyl group is equatorial and the other is axial. Draw the alternative chair conformation and calculate the ratio of the two conformations at 25°C.
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Starting from the wedge-and-dash structure below, rotate the
back carbon to provide the Newman projection in the most
stable conformation.
H₂C
H
(H3C) 3C
H
H
CH3
→
Starting from the wedge-and-dash structure below, rotate the
back carbon to provide the Newman projection in the most
stable conformation.
H3C
H
Br
H
H3C
H
Q
Following is a planar hexagon representation for one isomer of
1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this
compound and state which of the two is more stable.
H,C
CH3
H
H
H
CH3
Chapter 2 Solutions
Organic Chemistry
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- Following are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used solvent for organic compounds. Piperidine is found in small amounts in black pepper (Piper nigrum). (a) Complete the Lewis structure of each compound by showing all unshared electron pairs. (b) Predict bond angles about each carbon, oxygen, and nitrogen atom. (c) Describe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.arrow_forwardFollowing is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.arrow_forwardmyo-Inositol, one of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-inositol.arrow_forward
- 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?arrow_forwardFollowing is a structural formula for cortisol (hydrocortisone). Draw a stereo-representation of this molecule showing the conformations of the five- and six-membered rings.arrow_forwardBased on the given planar structure of 1,2,3-trichloro-4-methylcyclohexane, which of the following structures corresponds to the most stable chair conformation of the compound (Figure below)? CI 'CI CI CI CI CH3CI CI H3CZ CI CI CI H3CZ il CI CI CH3CIarrow_forward
- The molecule cis-1-bromo-4-isopropylcyclohexane can exist in two different chair conformations, which are interconvertible by means of a ring flip. Draw the most stable conformer.arrow_forwardStarting from the wedge-and-dash structure below, rotate the back carbon to provide the Newman projection in the most stable conformation. H3C H H3C H Br Harrow_forwardLooking alongC1−C2andC4−C5bonds, draw a Newman projection for each of the two chair conformations of trans 1,2-dimethylcyclohexane.arrow_forward
- Please draw three cis and trans 1,4-dimethylcyclohexane chair conformers and rank based on most to least stable.arrow_forwardConstruct a model of chloroethane, CH3CH2Cl. Remember that these models do not actually show the relative sizes of different atoms. View the model along the carbon-carbon axis and draw the sawhorse and Newman projections of the preferred conformation.arrow_forwardIdentify the correct chair conformations of the following compound and then indicate which one is more stable. OH OH OH HO 1 || 4 OI and II are correct chair structures and I is most stable OI and II are correct chair structures and II is most stable OI and III are correct chair structures and III is most stable O II and III are correct chair structures and II is most stable O II and III are correct chair structures and III is most stable |||arrow_forward
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