Concept explainers
Interpretation:
A molecular modeling kit is to be given to build a model of
Concept introduction:
In the case of disubstituted cyclohexane, the relationship between these two substituents with the ring is explained with the help of a Haworth projection. Since cyclohexane ring undergoes chair flipping with no switching of either substituent from their side, the relationship between these substituents on a cyclohexane ring does not change on flipping, that is, the cis substituents remain cis, and trans remain trans on flipping. In a Haworth projection, the ring is depicted as being planar, and bonds to substituents are drawn perpendicular to that plane in such way that these substituents come in the plane of the ring, and one side of the ring will be either above this plane or below this plane, depending on the rotation around the plane.
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Chapter 4 Solutions
ORGANIC CHEMISTRY PRINCIPLES & MECHANISM
- 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.arrow_forwardFollowing 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?arrow_forwardDraw the “chair twist" of the following molecules. Label the more stable conformation. Br •CH3 OH Draw planar models of the above molecules. Draw both chair conformation of the following molecule, and identify the most stable form. Me Me ....Et Mearrow_forward
- Q6. Draw both chair conformations for the following compound (Carbons atoms are numbered in the chair structures for your convenience. Idențify the more stable conformation.arrow_forwardDraw the Newman projection so that it corresponds to the molecule and conformation shown when viewed down the red bond in the direction of the arrow. Cl X H₂C H HS SHarrow_forwardneed help. Out of the four isomers shown above (menthol, isomenthol, neomenthol, and neoisomenthol), which isomer do you predict is the most stable? It may help to draw out each isomer in its most stable chair conformer to determine which has the most equatorial groups.arrow_forward
- Starting from the Newman projection below, rotate the back carbon to provide the structure in the least stable conformation. CH3 H Ø H CH3 CH3 H H H H H Harrow_forwardC. Using your molecular modeling kit, construct cis-1,4-dimethylcyclohexane. In the space below, draw one of the chair conformations. Label the methyl groups as either axial (a) or equatorial (e). Number the carbons of the cyclohexane ring, perform a chair flip and draw the new chair conformation.arrow_forwardCompare the following conformers of 1-fluoropropan-1-ol. Match each conformer to their corresponding relative energy. Recall, the more stable the conformer the lower the energy. OH CH3 'F 2. HOH 2nd Highest Energy H 2nd Lowest Energy H3C 3. H. ОН Lowest Energy H 'F Highest Energy ČH3 4. H3C, OH 'F 1. >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 is the most stable conformation of the following compound? HO CI HO. Но. HO. OH II II IVarrow_forwardIn the most stable chair conformation of the cyclohexane below, how many methyl groups would be axial? CH3 CH3 three zero two all four CH3 CH3arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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