III. For each structure, slight along the C2-C3 bond, draw the Newman projection of the MOST stable andLEAST stable conformations.Compound2-MethylbutaneLEAST stableNo.MOST stable12.3-Dimethylbutane32,2-Dimethylbutane3-Methyloctane2,3,4-Trimethylhexane

We have to draw the most stable and least stable conformation in Newman Projection of the following…

Answered: II. For each structure, slight along…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter3: Organic Compounds: Alkanes And Their Stereochemistry

Section3.SE: Something Extra

Problem 52AP: Increased substitution around a bond leads to increased strain. Take the four substituted butanes...

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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?
Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.
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.
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.
A 1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group axial and one group equatorial. Explain.
Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3-5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained? (a) 2-Methylbutane (b) 2,2-Dimethylbutane (c) 2,3-Dimethylbutane (d) 2,2,3-Trimethylbutane
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
6. Consider the following Newman Projections. Which is the most stable conformation? Which is the least stable? Why? H3CB CH3 CH3 H. H. Br H. CH3 H CH3 CH3 Br H B C
By considering viewed through the C-2-C-3 bond, which below conformations of 2,3- dibromobutane show the most stable and the least stable conformation? Clearly explain the reason, why? S CH3 H H Br. H3C, Br H3C Br Br Br H. Br CH3 ČH3 H I II III Br Br H3C, Br H3C H. H3C" H. Br ČH3 IV V
What structure represents the most stable conformation of cis-1,3-dimethylcyclohexane? CH3 H CH3 CH3 H. H H3C- CH3 H3C H I II III H H -CH3 CH3 H3C- H3C- H IV V
3. Draw both chair conformations for the cyclohexane molecule shown below, and circle the most stable conformation (the methyl group is larger than the hydroxyl group). OH H3C
Starting from the Newman projection below, rotate the back carbon to provide the structure in the least stable conformation. CH3 H Ø H CH3 CH3 H H H H H H

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II. For each structure, slight along the C2-C3 bond, draw the Newman projection of the MOST stable and LEAST stable conformations. Compound 2-Methylbutane MOST stable LEAST stable No. 1 2 2.3-Dimethylbutane 2,2-Dimethylbutane