Consider the three structures. 1,1-dimethylcyclobutane (a) Which of these structures has the most angle strain? 1,1-dimethylcyclobutane 1,1,3,3,5,5-hexamethylcyclohexane 1,1,3,3,5,5-hexamethylcyclohexane staggered butane (c) Which of these structures has the most torsional (eclipsing) strain? 1,1,3,3,5,5-hexamethylcyclohexane 1,1-dimethylcyclobutane staggered butane staggered butane H HI H3C staggered butane H H (b) Which of these structures has the most steric strain? 1,1-dimethylcyclobutane CH3 1,1,3,3,5,5-hexamethylcyclohexane

Consider the three structures. 1,1-dimethylcyclobutane (a) Which of these structures has the most angle strain? 1,1-dimethylcyclobutane 1,1,3,3,5,5-hexamethylcyclohexane 1,1,3,3,5,5-hexamethylcyclohexane staggered butane (c) Which of these structures has the most torsional (eclipsing) strain? 1,1,3,3,5,5-hexamethylcyclohexane 1,1-dimethylcyclobutane staggered butane staggered butane H HI H3C staggered butane H H (b) Which of these structures has the most steric strain? 1,1-dimethylcyclobutane CH3 1,1,3,3,5,5-hexamethylcyclohexane

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 2.49P: Use your answers from Problem 2.48 to complete the table showing correlations between cis,trans and...

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Consider the three structures. 1,1-dimethylcyclobutane 1,1,3,3,5,5-hexamethylcyclohexane staggered butane H H3C CH3 (a) Which of these structures has the most angle strain? (b) Which of these structures has the most steric strain? staggered butane 1,1-dimethylcyclobutane 1,1-dimethylcyclobutane 1,1,3,3,5,5-hexamethylcyclohexane 1,1,3,3,5,5-hexamethylcyclohexane staggered butane (c) Which of these structures has the most torsional (eclipsing) strain? O 1,1-dimethylcyclobutane 1,1,3,3,5,5-hexamethylcyclohexane staggered butane
Ill Consider the three structures. 1,1,3,3,5,5-hexamethylcyclohexane staggered butane 1,1-dimethylcyclobutane H. CH3 (a) Which of these structures has the most angle strain? (b) Which of these structures has the most steric strain? O 1,1-dimethylcyclobutane O 1,1,3,3,5,5-hexamethylcyclohexane O staggered butane O 1,1-dimethylcyclobutane O 1,1,3,3,5,5-hexamethylcyclohexane O staggered butane (c) Which of these structures has the most torsional MacBook Air 000 000 F7 F5 F8 F10 % 8 } K. 7. B. W
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11. s) Draw the most stable conformation of 1,3-dichloro-2,4-difluorocyclohexane: 12. Which of the following represents the most stable conformation of 1,2,4,5- tetramethyleyclohexane? (one correct answer) CH b) CH HC H- H- CH HC CH, CH 6. Give IUPAC name for the following molecule. Include "cis" and "trans" designations if applicable. H2C-CH3 H -CH2 H- H Br
Place the methyl group and hydrogen atom on the structures below to depict the conformation of cis- and trans-1-isopropyl-3- methylcyclohexane. CH3 CH(CH2)3 CH(CH2)3 Highest Energy cis-1-isopropyl-3- methylcyclohexane Lowest Energy trans-1-isopropyl-3- methylcyclohexane
1. Chair Strain (a) Consider (1R,2S,3S,4S)-1,4-dibromo-2-(tert-butyl)-3-methylcyclohexane. Circle the location (axial or equatorial) for each substituent in this molecule's most stable chair conformer. (b) (၁) Br 1-Br axial equatorial *Bu tBu axial equatorial "CH3 CH 3 axial equatorial Br 4-Br axial equatorial Draw the most stable chair conformer, adding only the substituents (not the hydrogen groups of those stereocenters) onto the chair below. Complete the table below, indicating how many of each type of interaction is present in total for the most stable chair conformer as described in (a). gauche interactions between gauche interactions 1,3-diaxial interactions substituents and the ring between substituents between substituents
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.
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
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?
For the attached question (a), do the positions of the H and CH3 of the back carbon matter? Can they be switched since the front carbon is 'symmetrical' with two hydrogens?
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Citing down the C3-C4 bond, and using the drawings below, complete the Newman projections for all staggered and eclipsed conformations of hexane. Which staggered conformation has the lowest energy? Which eclipsed conformation has the highest energy?