Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 8, Problem 28P
Interpretation Introduction
Interpretation:The reason for much greater existence of 1,2-ethanediol in the gauche conformation as compared to 1,2-dichloroethane needs to be explained. Whether the ratio of gauche:anti conformation of 2-chloroethanol is similar to that of 1,2-dichloroethane or 1,2-ethanediol needs to be determined.
Concept Introduction:The molecular formula of organic compound represents the number of bonded atoms with their atomic symbols. The structural formula represents all the bonded atoms with
Conformation isomers have same bonding of atoms or group but they have different orientation of groups in three dimension due to C-C bond rotation.
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Sketch a potential energy diagram for rotation around a carbon–carbon bond in propane. Identify each potential energy maximum and minimum with a structural formula that shows the conformation of propane at that point. Does your diagram more closely resemble that of ethane or of butane? Would you expect the activation energy for bond rotation in propane to be more than or less than that of ethane? Of butane?
Following is a staggered conformation for one of the enantiomers of 2-butanol
Q. Is this (R)-2-butanol or (S)-2-butanol?
Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq.
Chapter 8 Solutions
Organic Chemistry: Structure and Function
Ch. 8.1 - Prob. 8.1ECh. 8.1 - Prob. 8.2ECh. 8.3 - Prob. 8.4TIYCh. 8.3 - Prob. 8.5ECh. 8.3 - Prob. 8.6ECh. 8.4 - Prob. 8.7ECh. 8.5 - Prob. 8.8ECh. 8.5 - Prob. 8.9ECh. 8.5 - Prob. 8.10ECh. 8.5 - Prob. 8.11E
Ch. 8.5 - Prob. 8.12ECh. 8.6 - Prob. 8.14TIYCh. 8.7 - Prob. 8.15ECh. 8.7 - Prob. 8.16ECh. 8.8 - Prob. 8.18TIYCh. 8.8 - Prob. 8.19ECh. 8.8 - Prob. 8.21TIYCh. 8 - Prob. 24PCh. 8 - Prob. 25PCh. 8 - Prob. 26PCh. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - Prob. 30PCh. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - Prob. 38PCh. 8 - Prob. 39PCh. 8 - Prob. 40PCh. 8 - Prob. 41PCh. 8 - Prob. 42PCh. 8 - Prob. 43PCh. 8 - Prob. 44PCh. 8 - Prob. 45PCh. 8 - Prob. 46PCh. 8 - Prob. 47PCh. 8 - Prob. 48PCh. 8 - Prob. 49PCh. 8 - Prob. 50PCh. 8 - Prob. 51PCh. 8 - Prob. 52PCh. 8 - Prob. 53PCh. 8 - Prob. 54PCh. 8 - Prob. 55PCh. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Prob. 58PCh. 8 - Prob. 59PCh. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - Prob. 65PCh. 8 - Prob. 66P
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- Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energyarrow_forwardAccount for the fact that among the chlorinated derivatives of methane, chloromethane has the largest dipole moment and tetrachloromethane has the smallest dipole moment.arrow_forwardC6H12 From the chair conformation, rotate about the carbon-carbon bonds of the ring to form a boat conformation. In the boat conformation carbon atoms 1 and 4 are both above (they could also both be below) the plane described by carbon atoms 2, 3, 5 and 6. Look through each of the C-C bonds in the cyclohexane ring. Do you observe any eclipsing interactions? If so, describe what atoms/substituents are eclipsing.arrow_forward
- On a cyclohexane ring, an axial carboxyl group has a conformational energy of 5.9 kJ (1.4 kcal)/mol relative to an equatorial carboxyl group. Consider the equilibrium for the alternative chair conformations of trans-1,4-cyclohexanedicarboxylic acid. Draw the less stable chair conformation on the left of the equilibrium arrows and the more stable chair on the right. Calculate DG0 for the equilibrium as written and calculate the ratio of the more stable chair to the less stable chair at 25°C.arrow_forwardThe structure of cis-3,5-dimethylpiperidine is shown below, without stereochemistry. In the most stable chair conformation, predict the orientation of the two methyl groups. In the sketchpad, draw the structure of cis-3,5-dimethylpiperidine .arrow_forwardSketch an energy diagram that shows a conformational analysis of 2,2-dimethylpropane. Does the shape of this energy diagram more closely resemble the shape of the energy diagram more closely resemble the shape of the energy diagram for ethane or for butane?arrow_forward
- Which of the statements below correctly describes the chair conformations of trans-1,4-dimethylcyclohexane? * The lower energy chair conformation contains two axial methyl groups. The two chair conformations are of equal energy. The higher energy chair conformation contains one axial methyl group and one equatorial methyl group. O The higher energy chair conformation contains two axial methyl groups. The lower energy chair conformation contains one axial methyl group and one equatorial methyl group.arrow_forwardWhat is the energy difference between the axial and equatorial conformations of cyclohexanol (hydroxcycyclohexane) and how do you find it?arrow_forwardDraw the conformational analysis of 1-bromobutane looking at the C1-C2 bond. Provide the appropriate names for each conformation.arrow_forward
- Draw structural formulas for the cis and trans isomers of hydrindane. Show each ring in its most stable conformation. Which of these isomers is more stable?arrow_forwardIn addition to more highly fluorinated products, fluorination of 2-methylbutane yields a mixture of compounds with the formula C5H10F2. Draw the structures of all the isomers with the formula C5H10F2 that would be produced and label with a star all the chiral centers present in their structures.arrow_forwardWhich of the statements below correctly describes the chair conformations of trans-1,3-diethylcyclohexane.* The lower energy chair conformation contains two axial ethyl groups. The lower energy chair conformation contains two equatorial ethyl groups The higher energy chair conformation contains two axial ethyl groups. The higher energy chair conformation contains two equatorial ethyl groups. O The two chair conformations are equal in energy.arrow_forward
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