Concept explainers
(a)
Interpretation:
For each of the given molecule, the correct dash-wedge structure is to be drawn.
Concept introduction:
In Newman projection, the two atoms directly connected by the bond of interest are shown clearly. The nearer atom is represented as a point, and the more distant atom is represented as a circle. Bonds to the front atom meet at the point whereas bonds to the back atom connect to the circle.
(b)
Interpretation:
For each of the given molecule, the corresponding Haworth projection is to be drawn.
Concept introduction:
While drawing Haworth projection, the relationship of each substituent to the plane of the ring needs to be considered. In a Haworth projection, the ring is represented as being planar, and bonds to substituents are drawn perpendicular to that plane.
(c)
Interpretation:
It is to be determined, for each given molecule, whether the given conformation is most stable.
Concept introduction:
Each substituent on a cyclohexane ring is more stable in an equatorial position than in an axial position. More space is available on equatorial position than axial position. Therefore, the diequatorial conformer is more favorable over the diaxial conformer.
(d)
Interpretation:
For the given each molecule, the Newman projection of the molecule whose conformation is not the most stable conformation, is to be drawn.
Concept introduction:
Each substituent on a cyclohexane ring is more stable in an equatorial position than in an axial position. More space is available on equatorial position than axial position. Therefore, the diequatorial conformer is more favorable over the diaxial conformer.
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ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
- 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.arrow_forwardConsider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forwardOn the substituted cyclohexane, click on the two groups that are experiencing the largest 1,3-diaxial interaction. (Click on the groups themselves, not on bonds.) Then answer the question about this chair conformation.arrow_forward
- Draw the Newmann projections of this molecule along the circled bond of this molecule, from the point of view of the eye. You should include and label the syn-periplanar, gauche, anticlinal and anti-periplanar conformations, and whether the conformation is staggered or eclipsed. List these four conformations from most stable to least stable?arrow_forwardUse flat representation of rings, not chair in the drawing. Determine the most and least stable. Consider the most stable chair for each of these isomers, and then draw the most stable and least stable isomer based on a comparison of the best chair for each one.arrow_forwardWhich is the most stable stereoisomer and configuration of 1-chloro-4-methylcyclohexane between the cis and trans configurations? Please explain. Provide chair structures + show all H for cis- and trans-1-chloro-4-methylcyclohexane, and use arrows to show where steric strain occurs.arrow_forward
- What is the conformation of ring A? of ring B? of ring C? of ring D?arrow_forwardThe highest energy conformation of ethane has 12 kJ/mol of strain. The two highest conformations of butane have 16 and 19 kJ/mol of strain, respectively. How much strain does the highest energy conformation of 2,3-dimethylbutane have?arrow_forwardConsider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?arrow_forward
- Which chair conformation is more stable? Is it the right because bromine has a larger mass than a methyl group? Or is it the left because the methyl group has three hydrogens stemming from the carbon and is therefore ‘bulkier?’arrow_forwardStereoisomers share the same connectivity and differ only in the way their atoms are arranged in space. Draw the structure of a compound that is a stereoisomer of trans-1,2-dibromocyclobutane.(Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.)Use the wedge/hash bond tools to indicate stereochemistry where it exists.In cases where there is more than one answer, just draw one.arrow_forwardIs the 1st compound ( more, less or equally) stable than B? Pls show through illustrations of chair conformationsarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning