Custom eBook for Organic Chemistry
2nd Edition
ISBN: 9798214171104
Author: Straumanis
Publisher: Cengage Custom
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Chapter 7, Problem 14CTQ
Interpretation Introduction
Interpretation: The numbering of the carbon needs to be completed in the given chair flip.
Concept Introduction:
The chair conformation of cyclohexane is represented as follows:
During the flipping, no bond is break. The numbering in the chair form is represented as follows:
During ring flipping, mirror image of the chair conformation is formed.
It is represented as follows:
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4. For the following structures, draw both possible chair
conformations, using a ring flip to go from one to the other, and
circle the one that is most stable/lowest energy. (Hint: Use
Table 4.8 in Klein.) Show all groups, including hydrogen atoms,
attached to the cyclohexane ring.
А.
Me
Me
Et
В.
Et
t-Bu
Et
Q2. a) Draw the Newman projection of the most stable staggered conformation of 2-methylpentane,
looking down the 3,4 bond.
H3C
c-CH2-CH2CH3
H3C´H
b) The structure of cis-1-tert-butyl-3-methylcyclohexane is shown below. Draw both chair forms of
this molecule, and circle the one you think is less stable.
Me
't-Bu
Solve it please...
Chapter 7 Solutions
Custom eBook for Organic Chemistry
Ch. 7 - Prob. 1CTQCh. 7 - Prob. 2CTQCh. 7 - Prob. 3CTQCh. 7 - Draw wedge and dash skeletal representations of...Ch. 7 - Label each ring in Figure 7.2 cis or trans.Ch. 7 - Prob. 6CTQCh. 7 - Prob. 7CTQCh. 7 - Prob. 8CTQCh. 7 - a model of cyclohexane in a chair conformation,...Ch. 7 - Prob. 10CTQ
Ch. 7 - Prob. 11CTQCh. 7 - Fill in the blanks: cis-1,3-Dimethylcyclohexane...Ch. 7 - Prob. 13CTQCh. 7 - Prob. 14CTQCh. 7 - Prob. 15CTQCh. 7 - Prob. 16CTQCh. 7 - Prob. 17CTQCh. 7 - Prob. 18CTQCh. 7 - Draw chair representations of...Ch. 7 - Which stereoisomer in the previous question is...Ch. 7 - Prob. 21CTQCh. 7 - Prob. 1ECh. 7 - Label each of the following as cis, trans or...Ch. 7 - Which pair has more in common with one another?Ch. 7 - Prob. 4ECh. 7 - Prob. 5ECh. 7 - Prob. 6ECh. 7 - Fill in the table by drawing a representation of a...Ch. 7 - Prob. 9ECh. 7 - True or False: If you perform a chair flip on...Ch. 7 - Prob. 11ECh. 7 - Prob. 12ECh. 7 - Prob. 13ECh. 7 - Prob. 14ECh. 7 - Prob. 15ECh. 7 - Draw trans-1-tert-butyl-3-methylcyclohexane in its...Ch. 7 - Build a model of methylcyclohexane, and use the...
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- Use 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_forwardIn the box below give the Newman projection of the most stable conformer of the molecule shown below looking at the C2-C3 bond (in red). Place C2 in front. On the side list the energy strains that exist in that conformation. 3 CH3arrow_forwardhelp me pleasearrow_forward
- Please answer the question on the second photo by using the graph in the first photo.arrow_forwardFor the the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. 2,3-dimethylpentane ECLIPSING Interactions AB Energy kcal/mol H/H 1.0 H / Me 1.4 H/Et 1.5 H/i-Pr 1.6 H/t-Bu 3.0 Me / Me 2.6 Me / Et 2.7 Me/i-Pr 3.0 GAUCHE A. Interactions Me / Me Me / Et Me / i-Pr Me / t-Bu Et / Et Et / -Pr Et/t-Bu i-Pr/i-Pr B Energy kcal/mol 0.9 0.95 1.1 2.7 1.1 1.6 3.0 2.0arrow_forwardFor the the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. Lowest Energy Conformation 3-D sawhorse Newman ECLIPSING Interactions AB H/H H/Me H / Et H/i-Pr Energy kcal/mol 1.0 1.4 1.5 1.6 H/ t-Bu 3.0 Me / Me 2.6 Me / Et 2.7 Mei-Pr 3.0 GAUCHE A. Interactions Me / Me Me / Et Me / i-Pr Me / t-Bu Et / Et Et/i-Pr Et / t-Bu i-Pr/i-Pr 3-D sawhorse Energy kcal/mol Newman 0.9 0.95 1.1 2.7 1.1 1.6 Highest Energy Conformation 3.0 2.0arrow_forward
- 4. Clearly draw both Chair Conformations. of the following molecule Xordin 5. for the Molecule in Question 4 - Circle the lowest energy Chair Conformat. TAM!arrow_forward3)- Determine the total number of conformers and draw the Chair Structures of the conformers for the Tri-substituted cyclohexane structure given below (i.e., "A"). Draw the relative energy diagram for the possible conformers for the cyclohexane structure below. Note, draw only the required structures for the conformers of A. Also, include hydrogen atoms wherever there are substituents on all of your chair conformers. Answer (Total #of Conformers): Chair Structures: Relative Energy Diagram 8 bas roll 3arrow_forwardGiven cyclohexane in a chair conformation, construct the more stable conformation of cis‑1‑methyl‑2‑propylcyclohexane by filling in the missing atoms or groups. Use the numbering provided on the ring.arrow_forward
- I don't understand why the first one and second one are cis and trans respectively. Wouldn't the first one be trans-1,2-dimethylcyclobutane because the torsional strain wouldn't allow the carbons to be in the same conformation. Meaning one of the carbons would be up and then the next would be down and so on. Since both methyl groups are equatorial and the first and second carbons are arranged up and down, wouldn't it be trans. Same logic for the second molecule. Carbon 1, which is attached to the methyl is down, carbon 3 which is attached to the methyl should be down also because of torsional strain, and since both methyl are in axial (or equatorial?), it would be cis. Or is it based off of the way the carbons are positioned in the picture?arrow_forward- Consider 1-bromopropane(propyl bromide). I) Draw a Newman projection (conformation) in which methyl and bromine are anti. II) Draw a Newman projection (conformation) in which methyl and bromine are in gauche. II) Draw a Newman projection (conformation) which represents the least stable eclipsed conformation.arrow_forwardFor the 1,2-dichlorocyclohexane stereoisomers, which conformation of the trans stereoisomer has the lower energy, the diaxial or the diequatorial conformer? Which isomer and conformation of the three you built has the lowest energy? E of all the isomers of 1,2-dichlorocyclohexane. Explain the differences in energy, i.e., identify the sources of strain in the conformations you built. Show the sources of strain in a drawing.arrow_forward
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