Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 7, Problem 17E
Build a model of methylcyclohexane, and use the model to complete the following Newmanprojections of methylcyclohexane in the chair conformation:
a. When the methyl group is in an axial or equatorial (circle one) position, the molecule is inits lowest potential energy conformation.
b. Label one Newman projection above anti and the other gauche to describe the relationshipbetween the methyl group and
c. In general, which is a lower PE conformation, anti or gauche?
d. Explain how your answer to b and c provide an explanation for why it is more favorable fora large group to be in an equatorial than an axial position.
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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
CH3
For 1,2-dichloroethane:
a.Draw Newman projections for all eclipsed conformations formed by rotation from 0° to 360° about the carbon-carbon single bond.
b.Which eclipsed conformation(s) has (have) the lowest energy? Which has (have) the highest energy?
c.Which, if any, of these eclipsed conformations are related by reflection?
Sighting along the appropriate C-C bond of neopentane C(CH3)4:
a) Draw its Newman projections.
b) How much energy does the most unstable conformation possess?
c) Make the energy diagram for the different conformers.
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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- Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.arrow_forwardConsider 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_forwardUse your answers from Problem 2.48 to complete the table showing correlations between cis,trans and axial,equatorial for disubstituted derivatives of cyclohexane. Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3-dimethylcyclohexane, 1,4-dimethylcyclohexane. (a) Indicate by a label whether each methyl group is axial or equatorial.arrow_forward
- Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.arrow_forwarda model of cyclohexane in a chair conformation, and explain why the names “axial” and“equatorial’ are appropriate.arrow_forwardDraw alternative chair conformations for the following substituted cyclohexane and determine which chair is more stable. C HO H ОН In its most stable chair conformation, indicate the orientation of each of the labeled groups in this substituted cyclohexane. Group a: Group b: Group c:arrow_forward
- 5. (a) Identify the relationship of the two compounds below. (b) Write the most stable chair conformation for each. Br CH₂ and A. identical B. constitutional isomers C. stereoisomers D. unrelated Br CH₂arrow_forward3. Draw both chair conformations for the cyclohexane molecule shown below, and circle the most stable conformation (the methyl group is larger than the hydroxyl group). OH H3Carrow_forward6. Consider the following Newman Projections. Which is the most stable conformation? Which is the least stable? Why? H3CB CH3 CH3 H. H. Br H. CH3 H CH3 CH3 Br H B Carrow_forward
- 5a. Draw a Newman Projection for the following compound. 5b. Rotation about the C3 – C4 bond in conformer 1 leads to two less stable staggered conformers. Draw a Newman Projection for one of these less stable conformers, as viewed down the C3 to C4 bond. What is the single highest energy gauche interaction in the Newman Projection?arrow_forward3.) 2-Methylbutane (isopentane) is used, in conjunction with liquid nitrogen, to freeze tissues for cryosectioning in histology. Below is the potential energy diagram for all the conformers of 2-methylbutane. Provide structures that match structure A, B, and C in the boxes provided. B F IM C A potential energy Conformer A 0° D angle of internal rotation Conformer B E F H 360° (=0°) Conformer Carrow_forwardWhich of the following is the Newman projection of the most stable conformation of 2,3,4-trimethylpentane as you look down the bond between carbons 2 and 3? 8. CH3 H;C. a) CH3 H,C CH3 H H;C. CH3 H3C b) c) d) H3C CH3 H CH(CH3)2 CH3 H CH3 H `CH,CH3 CH(CH3)2 CH3 CH3arrow_forward
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