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
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
2. Chair Strain
(a)
Consider the following cyclohexane derivative. Circle the location (axial or
for each substituent in this molecule's most stable chair conformer.
F
axial
equatorial
Br
axial
equatorial
Bru
CH3
Ph
axial
equatorial
Ph
CH3
axial
equatorial
equatorial)
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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- Please answer fast I give you upvote.arrow_forwardFor 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_forward2. Chair Strain (a) Consider the following cyclohexane derivative. Circle the location (axial or for each substituent in this molecule's most stable chair conformer. (b) (c) ( F axial equatorial Br axial equatorial Br CH3 Ph axial equatorial Ph CH3 axial equatorial equatorial) Draw the chair conformer described in (a), adding only the substituents (not the hydrogen groups of those stereocenters) onto the template below. O Complete the table, indicating how many of each type of interaction is present in total for the chair conformer described in (a). gauche interactions between gauche interactions substituents and the ring between substituents 1,3-diaxial interactions between substituents (d) ( Draw the other conformer that results from a chair flip onto the template below. Ma the changes that happen in the chair flip, but don't make other changes. Only draw substituerarrow_forward
- Solve it please...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_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_forward
- 6. 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_forwardhelp me pleasearrow_forwardPlease answer the question on the second photo by using the graph in the first photo.arrow_forward
- 1. (6 points) Draw clear pictures showing the two chair conformations of this compound. Circle the lower energy (more stable) conformation or write "same energy". ||| |||arrow_forwardAn explanation would really help,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_forward
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