Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 4, Problem 55P
For each compound drawn below:
a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring and wedges and dashed wedges for substituents.
b. Draw the two possible cahir conformations for the cis isomer. Which conformation, if either, is more stable?
c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?
d. Which isomer, cis or trans, is more stable and why?
[1] 
[2] 
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Consider 1,2-dimethylcyclohexane.a. Draw structures for the cis and trans isomers using a hexagon for the six-membered ring.b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?d. Which isomer, cis or trans, is more stable and why?
For each compound drawn below:
a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashed wedges for substituents.
b.Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?
c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?
d.Which isomer, cis or trans, is more stable and why?
Consider 1,2-dimethylcyclohexane.
a.Draw structures for the cis and trans isomers using a hexagon for the sixmembered ring.
b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?
c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?
d.Which isomer, cis or trans, is more stable and why?
Chapter 4 Solutions
Organic Chemistry (6th Edition)
Ch. 4.1 - Prob. 1PCh. 4.1 - Problem 4.2 Which of the following is not another...Ch. 4.1 - Problem 4.3 Draw the five constitutional isomers...Ch. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.2 - Draw the five constitutional isomers that have...Ch. 4.4 - Problem 4.7 Give the IUPAC name for each...Ch. 4.4 - Give the IUPAC name for each compound. a....Ch. 4.4 - Problem 4.9 Give the structure corresponding to...Ch. 4.4 - Prob. 10P
Ch. 4.5 - Give the IUPAC name for each compound.Ch. 4.5 - Give the structure corresponding to each IUPAC...Ch. 4.8 - Arrange the following compounds in order of...Ch. 4.9 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4.9 - Prob. 15PCh. 4.9 - Prob. 16PCh. 4.10 - Problem 4.17 a. Draw the three staggered and...Ch. 4.10 - Problem 4.18 Rank the following conformations in...Ch. 4.10 - Problem 4.19 Consider rotation around the...Ch. 4.10 - Calculate the destabilization present in each...Ch. 4.12 - Problem 4.21 Classify the ring carbons as up or...Ch. 4.12 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4.13 - Draw a second chair conformation for each...Ch. 4.13 - Problem 4.24 Draw both conformations for and...Ch. 4.13 - Problem 4.25 Draw the structure for each compound...Ch. 4.13 - Prob. 26PCh. 4.14 - Prob. 31PCh. 4.14 - Prob. 32PCh. 4.15 - Prob. 33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 42PCh. 4 - 4.46 Considering rotation around the bond...Ch. 4 - 4.50 Calculate the barrier to rotation for each...Ch. 4 - 4.51 The eclipsed conformation of is less...Ch. 4 - (a) Draw the anti and gauche conformations for...Ch. 4 - For each compound drawn below: a.Label each OH,Br...Ch. 4 - Draw the two possible chair conformations for...Ch. 4 - For each compound drawn below: a. Draw...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 66PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 72PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 74PCh. 4 - Prob. 75PCh. 4 - Consider the tricyclic structure B (a) Label each...Ch. 4 - Read Appendix B on naming branched alkyl...Ch. 4 - Read Appendix B on naming bicyclic compounds. Then...
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- Use 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_forwardLabel each ring in Figure 7.2 cis or trans.arrow_forwardIn the next chapter we'll look at cycloalkanes—saturated cyclic hydrocarbons—and we’ll see that the molecules generally adopt puckered, nonplanar conformations. Cyclohexane, for instance, has a puckered shape like a lounge chair rather than a flat shape. Why?arrow_forward
- For each compound drawn below: a. Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashes for substituents. b. Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable? c. Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable? d. Which isomer, cis or trans, is more stable and why? [1] [2] [3]arrow_forwardAnswer the following questions and upload your answer. A. Draw the two chair conformations of cis-1-isopropyl-3-methylcyclohexane. Write under your drawing which conformation is the most stable one. B. Would the trans isomer be more stable than the cis isomer? Why?arrow_forwarda) Draw the two ring flipped conformers of each molecule A and B. Indicate the more stable conformer, respectively. CH3 fCH3 H,C. CH3 H3C. CH3 CI CI A B a) Which is more stable between A and B? Why?arrow_forward
- Which is more stable and why? II A. I because it has a chair conformation with the most axial bonds B. I because it has a chair conformation with the most equatorial bonds C. II because it has a chair conformation with the most axial bonds OD. II because it has a chair conformation with the most equatorial bonds %3Darrow_forwardFor 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?arrow_forwardWhich statement is true about these conformers? H. H. H H CH3 H3C H. H,C H,C H. H. A O A and B are equally stable O Difficult to predict O A more stable than B ) B more stable thanarrow_forward
- Draw a model of ethane. Imagine rotating the C-C single bond. a. Is there a change in the relative positions of the different atoms as the C-C bond is rotated? Yes or No? b. Does the ethane molecule have more than one conformation? Yes or No?arrow_forwarda. Using the wedge-and-dash notation, draw the nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane. b. From the nine stereoisomers, identify one pair of enantiomers. c. Draw the most stable conformer of the most stable stereoisomer.arrow_forwardFor each attached compound drawn below:a.) Draw representations for the cis and trans isomers using a hexagon for the six-membered ring, and wedges and dashed wedges for substituents.b.) Draw the two possible chair conformations for the cis isomer. Which conformation, if either, is more stable?c.) Draw the two possible chair conformations for the trans isomer. Which conformation, if either, is more stable?d.) Which isomer, cis or trans, is more stable and why?arrow_forward
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