Loose Leaf for Organic Chemistry
10th Edition
ISBN: 9781259626548
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education (edition 10)
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Textbook Question
Chapter 4, Problem 27P
Including stereoisomers, write structural formulas for all of the compounds that are
trichloro derivatives of
Cyclobutane
Cyclopentane
Which are chiral? Which are achiral?
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Between the cis and trans configuration of 1-chloro-4-methylcyclohexane, which is the most stable stereoisomer and configuration? To prove your argument, draw a model or use a modeling software to model cis- and trans-1-chloro-4-methylcyclohexane (show all the hydrogens and ensure proper chair conformation) and use arrows to show where steric strain occurs.
Between the cis and trans configuration of 1-chloro-3-methylcyclohexane, which is the most stable stereoisomer and configuration? To prove your argument, use your models or a modelling software to model cis- and trans-1-chloro-3-methylcyclohexane (show all the hydrogens and ensure proper chair conformation) and use arrows to show where steric strain occurs. Include these photos in your answer.
Which do you expect to be the more stable conformation of cis-1,3-dimethylcyclobutane, A or B? Why?
Chapter 4 Solutions
Loose Leaf for Organic Chemistry
Ch. 4.2 - Examine the following for chirality centers:Ch. 4.2 - Prob. 2PCh. 4.3 - Prob. 3PCh. 4.3 - Prob. 4PCh. 4.4 - Prob. 5PCh. 4.4 - Prob. 6PCh. 4.5 - Does the molecular model shown represent...Ch. 4.6 - Assign absolute configurations as R or S to each...Ch. 4.6 - Draw three-dimensional representations ofCh. 4.7 - Prob. 10P
Ch. 4.7 - Using the Fischer projection of (R)-2-butanol...Ch. 4.8 - Prob. 12PCh. 4.9 - Prob. 13PCh. 4.9 - Prob. 14PCh. 4.10 - Prob. 15PCh. 4.10 - Draw Fischer projections of the four...Ch. 4.10 - Prob. 17PCh. 4.11 - A meso stereoisomer is possible for one of the...Ch. 4.11 - One of the stereoisomers of...Ch. 4.12 - Prob. 20PCh. 4.12 - Prob. 21PCh. 4.13 - Prob. 22PCh. 4.13 - Prob. 23PCh. 4.13 - Prob. 24PCh. 4.14 - Prob. 25PCh. 4 - Prob. 26PCh. 4 - Including stereoisomers, write structural formulas...Ch. 4 - Prob. 28PCh. 4 - Prob. 29PCh. 4 - Prob. 30PCh. 4 - Prob. 31PCh. 4 - Prob. 32PCh. 4 - Prob. 33PCh. 4 - Prob. 34PCh. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - Prob. 37PCh. 4 - Prob. 38PCh. 4 - Prob. 39PCh. 4 - (-)-Menthol is the most stable stereoisomer of...Ch. 4 - Prob. 41PCh. 4 - Prob. 42PCh. 4 - (a) An aqueous solution containing 10 g of...Ch. 4 - Prob. 44DSPCh. 4 - Prob. 45DSPCh. 4 - Consider two chemical changes: one occurring at a...Ch. 4 - Consider two chemical changes: one occurring at a...Ch. 4 - Prob. 48DSPCh. 4 - Consider two chemical changes: one occurring at a...Ch. 4 - Consider two chemical changes: one occurring at a...
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- Pentalene, azulene, and heptalene are conjugated hydrocarbons that do not contain a benzene ring. Which hydrocarbons are especially stable or unstable based on the number of π electrons they contain? Explain your choices.arrow_forwardBelow are two conformers of trans-1-tert-butyl-3-methylcyclohexane. As shown in the equilibrium, conformer 1 is more favored by nature. Explain this phenomenonarrow_forwardStereoisomers share the same connectivity and differ only in the way their atoms are arranged in space. Draw the structure of a compound that is a stereoisomer of trans-1,2-dibromocyclobutane.(Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.)Use the wedge/hash bond tools to indicate stereochemistry where it exists.In cases where there is more than one answer, just draw one.arrow_forward
- calculate the difference in energy between the two conformations of trans-4-tert-butyl-1-methylcyclohexane?arrow_forwardcalculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer predominates at equilibrium?arrow_forwardGive a clear explanation handwritten answer..give the stereochemistry with most stable chair conformation of trans-1,3-dimethylcyclohexane...arrow_forward
- Consider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy 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_forwardUsing what you know about the conformational energetics of substituted cyclohexanes, predict which of the two decalin isomers is more stable. Explain your reasoning.arrow_forward
- On the substituted cyclohexane, click on the two groups that are experiencing the largest 1,3-diaxial interaction. (Click on the groups themselves, not on bonds.) Then answer the question about this chair conformation.arrow_forwardHow the relative stability of the two conformations of any disubstituted cyclohexane can be analyzed ?arrow_forwardWhich is the most stable stereoisomer and configuration of 1-chloro-4-methylcyclohexane between the cis and trans configurations? Please explain. Provide chair structures + show all H for cis- and trans-1-chloro-4-methylcyclohexane, and use arrows to show where steric strain occurs.arrow_forward
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