Given the planar trisubstituted cyclohexane, fill in the missing substituents (with H or Cl) to complete the two possible cyclohexane chair conformations. Then, determine the more stable conformer. You might find it helpful to make a model of the cyclohexane to help visualize the chair conformations CI CI H. H. chair flip H. H. H. Answer Bank H. Chair 1 Chair 2 Cl H

Given the planar trisubstituted cyclohexane, fill in the missing substituents (with H or Cl) to complete the two possible cyclohexane chair conformations. Then, determine the more stable conformer. You might find it helpful to make a model of the cyclohexane to help visualize the chair conformations CI CI H. H. chair flip H. H. H. Answer Bank H. Chair 1 Chair 2 Cl H

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 1CTQ

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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?
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.
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.
In the next chapter we'll look at cycloalkanesâ€”saturated cyclic hydrocarbonsâ€”and weâ€™ll see that the molecules generally adopt puckered, nonplanar conformations. Cyclohexane, for instance, has a puckered shape like a lounge chair rather than a flat shape. Why?
4. Perform a conformational analysis on cyclohexane derivative I. Draw out both possible conformers and circle Using A, U, and G values estimate the energy difference (DG) the preferred (lowest energy) conformer between the two conformers and predict the approximate ratio of the two conformers at room temperature Hj C Br cyclohexane I
Draw the two chair cyclohexane conformations for the compound shown below. How many substituents are equatorial in the less stable conformation? CI" O معه O O 2 JI... CI ""CI
Consider pentane, C5H12. Looking through the internal C3-C4single bond, draw thesix Newman projections (where the angle between two bonds as you look through the C3and C4bond is either 0°or 60°of the different conformations. Label the conformers/rotamers using I, II, etc. a.Which conformer is the most stable? the least stable? b.Which rotamer is the anticonformer? the gaucheconformer? c.Draw the anticonformer in saw horse projection.
Given cyclohexane in a chair conformation, construct the more stable conformation of cis-1-ethyl-2-fluorocyclohexane by filling in the missing atoms or groups. Use the numbering provided on the ring. H. Answer Bank H 5 1 H. F H ethyl 3 H
4. a. Draw the two chair conformations for cis-1,4-dimethylcyclohexane. Use the given template. In the conformation on the left, all atoms bonded to carbon 1 have been drawn. You need to complete the rest of the structure. In the conformation on the right, fill in the two boxes at carbon 1 and complete the rest of the structure. CH3 H b. Identify the molecule for which the two chair conformations are expected to have the same energy. Completely fill in the circle in front of your choice. cis-1,3-dichlorocyclohexane cis-1,4-dichlorocyclohexane O trans-1,2-dichlorocyclohexane
ball & stick v + labels Which of the Newman structures below represents this conformation of 3-chloro-2-methylpentane, as viewed along the C2-C3 bond? ***** CH3 Et H Et Et. .CI H3C. CH3 Et. H3C. H3C H. TCI H3C CH3 H. ČH3 H ČH3 a b d (Enter the letter(s) of the correct structure(s), in alphabetical order and without punctuation; more than one answer may be correct. Et = an ethyl group)
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? CH3 H Br. H3C, Br H3C H3Č Br Br Br H. ČH3 Br CH3 H I II III Br Br Br H3C. H3C ČH3 H. H3C H. Br IV V
Analyze the two Newman projections and determine the relationship between the two. How would you describe the relation between conformations when they are maintained at a temperature too low to permit them to interconvert? CH3 CH3 Br. H H H H A. Identify the relationship. They are identical. They are structural isomers. They are stereoisomers. They are conformers. H H -I H Br H B. What is the relationship at low temperatures? They are identical. They are conformational diastereomers. They are structural isomers. They are conformational enantiomers.