Concept explainers
(a)
Interpretation:
To make model for compound A and draw the chair conformation, label as equatorial or axial and circle the most stable structure.
Concept Introduction:
Conformation is considered as the shape of molecule which it adopts when it rotates about its single or double bonds. When the molecule tries to take up the less strained position, it is the most stable form.
(b)
Interpretation:
To make model for compound B and consider the transannular and gauche interactions of its chair conformations and to elaborate the problems of conformation when compared to that of compound A.
Concept Introduction:
When a molecule tends to rotate about its single or double bonds, the molecule attains a specific shape based on its stability such that it has less strained position. This is said to be conformation.
When there is interaction between two non-bonding molecular groups in a large ring which are not adjacent, it is said to be trans annular. When the ring substitutes of the adjacent groups has a non- bonded interaction, it is said to be gauche interaction.
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Organic Chemistry: Structure and Function
- 5. Draw the two chair conformations ("ring filips") of trans –1- ethyl-4-methylcyclohexane to show the axial and equatorial substituents (including all hydrogens). Then determine which of the two conformations is more stable and why.arrow_forward4. 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 Iarrow_forwardConsider 1,2-dimethylcyclohexane. a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered ring. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d.Which isomer, cis or trans, is more stable and why?arrow_forward
- Connections to biology 6. Idose is a monosaccharide (i.e. sugar) molecule. The structure shown on the left below represents one form of idose in a six-membered ring. Draw the two chair conformations of this molecule using the templates. Note that the positions of carbon 1 are marked in all structures. OH HO 2 OH LO 1, OH OH OHarrow_forwardWhich of the following best explains the reason for the relative stabilities of the conformers shown? II. H3C CH3 I. H CH3 ... -H -- H. H3C H A I has more steric strain. B Il has more torsional strain. I has more torsional strain. D II has more steric strain.arrow_forwardWhich is more stable and why? II A. I because it has a chair conformation with the most axial bonds B. I because it has a chair conformation with the most equatorial bonds C. II because it has a chair conformation with the most axial bonds OD. II because it has a chair conformation with the most equatorial bonds %3Darrow_forward
- NAME: 1. Draw the 2 chai conformations of cis-1-tert-butyl-2-ethylcyclohexane. Circle the most stable conformation of the moleculearrow_forward4. Which structure below represents the most stable conformation of cis-1-t-butyl-4-methylcyclohexane? A B D 5. The planar form of which ring would have bond angles close to the tetrahedral value, but is destabilized by eclipsing interactions (torsional strain)? Which of the following statements about conformations is FALSE? A) Conformations can be isolated and separated at room temperature B) Conformations are interconverted by rotation about o-bonds C) For butane the staggered anti conformation is the most stable D) For ethane the eclipsed conformation is the least stable 6. 7. Which of the following compounds has two chirality centers? .H H. H3Carrow_forward6) Draw the energetically favored (more stable) chair conformer of the following cyclohexane. H3C OH 110arrow_forward
- Given the cyclohexane chair conformation and four similar compounds, identify the relationship of each structure to the chair conformation. CH3 H3C, B H. How is Compound B related to the chair conformation? O It is a conformation isomer (conformer). H3C H3C H O It is a constitutional isomer. O It is not an isomer. H. O It is a stereoisomer.arrow_forwarda) Draw the two chair conformations for the compound below, indicating which is more stable. OH CHO b) This molecule is a compound with an intense flowery odor used in perfumes, but it isomerizes rapidly in base to its odorless diastereoisomer. Draw the chair conformation of this diastereoisomer and explain why the isomerization occurs readily.arrow_forward5a. Draw a Newman Projection for the following compound. 5b. Rotation about the C3 – C4 bond in conformer 1 leads to two less stable staggered conformers. Draw a Newman Projection for one of these less stable conformers, as viewed down the C3 to C4 bond. What is the single highest energy gauche interaction in the Newman Projection?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning