Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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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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Students have asked these similar questions
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
In 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
CH3
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
Chapter 7 Solutions
Organic Chemistry: A Guided Inquiry
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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- For the most stable conformation of trans-1,2-dimethylcyclohexane1. One methyl with occupy an axial position and the other an equatorial position.2. Both methyl groups will occupy axial position.3. Both methyl groups will occupy equatorial position.arrow_forwardhelp me pleasearrow_forward6. Newman projections to Lewis structures From the following Newman projections, draw the corresponding Lewis structure in the same conformation. A) B) H. H CH3 H₂C N H OH CI Br CH3 H OH CH3arrow_forward
- a) i) Draw the Newman projections for the conformations of ethane (staggered and eclipsed) 2. Which is higher in energy? Which is more stable? 3. Next to each conformer, draw the equivalent ‘sideways’ view, using wedged bondsarrow_forwardtranslate the bond-line notation structure to the Newman projection by filling int the missing groups (A, B, C, D or E) on the lines in the Newman projection so they match the conformation given in the original structure. Circle if the conformation is a staggered or eclipsed.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. 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_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_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_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_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
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