3. Complete the chair conformations on the right by adding isopropyl groups in appropriate locations, so that the chair conformations correspond to the dash-wedge diagrams. In each case, circle the more stable chair conformation and explain why it is more stable Explanation 8

3. Complete the chair conformations on the right by adding isopropyl groups in appropriate locations, so that the chair conformations correspond to the dash-wedge diagrams. In each case, circle the more stable chair conformation and explain why it is more stable Explanation 8

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
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.
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.
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?
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.
Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.
myo-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.
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.
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
2. Convert the following hexagonal drawings into most stable chair conformation, and place them in indicated boxes below. Do not use wedge and dash in chair conformation. HO но... H3C CH3 CH3 ...ОН OH ОН ОН OH CH3 YOH CH3
Draw 1-methyl-3-isopropylcyclohexane in its most stable conformation. Hint: Please note that the most stable conformation of cychohexane is NOT a planar hexagon
Strain of one Strain of one 1,3-diaxial interaction 1,3-diaxial interaction Strain of one 1,3-diaxial interaction H X Ph (C6H5) CO,H CN F 0.12 Me 0.9 1.5 Cl 0.7 0.1 0.25 Et 0.95 Br 0.25 i-Pr 1.1 OH 0.5 t-Bu 2.7

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Cis/trans substituted planar form	Axial/equatorial relationship on chair conformation
1,2-cis disubstituted	a.e/e,a
1,2-trans disubstituted	a,a/e,e
1,3-cis disubstituted	a,a/e,e
1,3-trans disubstituted	a,e/e,a
1,4-cis disubstituted	a,e/e,a
1,4-trans disubstituted	a,a/e,e