Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 3, Problem 63P
For each of the following disubstituted cyclohexanes, indicate whether the substituents in its two chair conformers would be both equatorial in one chair conformer and both axial in the other or one equatorial and one axial in each of the chair conformers:
- a. cis-1,2-
- b. trans-1,2-
- c. cis-1,3-
- d. trans-1,3-
- e. cis-1,4-
- f. trans-1,4-
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Chapter 3 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 3.1 - Name each of the following:Ch. 3.1 - Draw the structures and name the four...Ch. 3.1 - Draw the structure for each of the following...Ch. 3.1 - Name the following compounds:Ch. 3.1 - Prob. 7PCh. 3.2 - What is each compounds systematic name?Ch. 3.2 - Prob. 11PCh. 3.3 - Prob. 12PCh. 3.3 - Convert the following condensed structures into...Ch. 3.3 - The molecular formula for ethyl alcohol (CH3CH2OH)...
Ch. 3.3 - Draw a condensed and a skeletal structure for the...Ch. 3.3 - What is each compounds systematic name?Ch. 3.4 - Prob. 17PCh. 3.4 - Give two names for each of the following alkyl...Ch. 3.5 - Are the following compounds primary, secondary, or...Ch. 3.5 - Name the following amines and tell whether they...Ch. 3.5 - Draw the structures and provide systematic names...Ch. 3.6 - Predict the approximate size of the following bond...Ch. 3.7 - What is the smallest straight-chain alkane that is...Ch. 3.7 - Prob. 24PCh. 3.7 - Prob. 25PCh. 3.7 - Prob. 26PCh. 3.7 - List the compounds in each set from highest...Ch. 3.8 - Rank the following compounds in each set from most...Ch. 3.8 - In which solvent would cyclohexane have the lowest...Ch. 3.8 - Prob. 30PCh. 3.9 - Prob. 31PCh. 3.9 - a. Draw the three staggered conformations and the...Ch. 3.9 - a. Draw the most stable conformation of pentane...Ch. 3.11 - Draw 1,2,3,4,5,6-hexachlorocyclohexane with a. all...Ch. 3.12 - At any one time, would you expect there to be more...Ch. 3.13 - Prob. 36PCh. 3 - a. How many hydrogens does an alkane with 17...Ch. 3 - Prob. 2PCh. 3 - Draw a condensed structure and a skeletal...Ch. 3 - Prob. 39PCh. 3 - Prob. 40PCh. 3 - Which of the following represents a cis isomer?Ch. 3 - a. How many primary carbons does each of the...Ch. 3 - Name the following amines and tell whether they...Ch. 3 - Which of the following conformers of isobutyl...Ch. 3 - What is each compounds name? a. CH3CH2CH2OCH2CH3Ch. 3 - Draw the structural formula for an alkane that has...Ch. 3 - Which has a. the higher boiling point:...Ch. 3 - Ansaid and Motrin belong to the group of drugs...Ch. 3 - A student was given the structural formulas of...Ch. 3 - Which of the following conformers has the highest...Ch. 3 - Prob. 51PCh. 3 - Draw skeletal structures for the following: a....Ch. 3 - Prob. 53PCh. 3 - For rotation about the C-3 8 C-4 bond of...Ch. 3 - Prob. 55PCh. 3 - What is each compounds systematic name?Ch. 3 - Draw the two chair conformers for each of the...Ch. 3 - Draw the nine constitutional isomers with...Ch. 3 - Prob. 59PCh. 3 - Prob. 60PCh. 3 - Prob. 61PCh. 3 - Using Newman projections, draw the most stable...Ch. 3 - For each of the following disubstituted...Ch. 3 - Prob. 64PCh. 3 - Prob. 65PCh. 3 - What is each compounds systematic name?Ch. 3 - Prob. 67PCh. 3 - Bromine is a larger atom than chlorine, but the...Ch. 3 - Prob. 69PCh. 3 - Prob. 70PCh. 3 - a. Draw a potential energy diagram for rotation...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- On the left is a stereorepresentation of glucose (we discuss the structure and chemistry of glucose in Chapter 25). (a) Convert the stereorepresentation on the left to a planar hexagon representation. (b) Convert the stereorepresentation on the left to a chair conformation. Which substituent groups in the chair conformation are equatorial? Which are axial?arrow_forwardWrite the energy diagram corresponding to each conformer by writing the confomers (and Newman projection formulas) formed by the rotation of the bond between the carbon 3 and 4 (C3 and C4) of the 2-methylpentane. Indicate the most stable and unstable confomers.arrow_forwardConsider the substituted cyclohexane shown in the ball-and-stick model.a.Label the substituents on C1, C2, and C4 as axial or equatorial. b. Are the substituents on C1 and C2 cis or trans to each other? c.Are the substituents on C2 and C4 cis or trans to each other? d.Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forward
- Consider the substituted cyclohexane shown in the ball-and-stick model.a. Label the substituents on C1, C2, and C4 as axial or equatorial.b. Are the substituents on C1 and C2 cis or trans to each other?c. Are the substituents on C2 and C4 cis or trans to each other?d. Draw the second possible conformation in the chair form, and classify it as more stable or less stable than the conformation shown in the three-dimensional model.arrow_forward1.1 Build a model for line structure and use the template given to draw a Newman projection for this conformation of the compound when viewed along the C2-C3 bond. (template given in second photo) 1.2 why is this the most stable structure?arrow_forwarda. Draw trans-1-ethyl-2-methylcyclohexane in its lowest energy conformation. Choose a chair from the Templates toolbar at the bottom. Make sure it’s the appropriate chair, including any heteroatoms. Replace the appropriate hydrogens with the appropriate −CH3−CH3 or other groups. b. Draw the structure that corresponds with the name: isobutylcyclopentane.arrow_forward
- Draw Newman projections for all the additional eclipsed and staggered conformations B, C, D, E and F, arising from rotation about the C1-C2 bond of 1,1-dichloropropane. Start with Newman projection A and rotate the front carbon clockwise in 60o steps in order to generate the other Newman projections. Sketch the energy profile diagram starting with Newman projection A, showing the relative energy levels of projections B through F. Write the letter designation of the conformation under each appropriate section of the energy profile diagram.arrow_forward1.Draw boat and chair forms of cyclohexane. Clearly indicate the axial and equatorialpositions on the chair form. Indicate which is more stable and give reasons for your answer 2. Draw chair forms for all possible stereoisomers of the following and write e IUPAC names and include cis-trans (a) Chlorocyclohexane (b) 1,2-Dichlorocyclohexane(c) 1,3-Dichlorocyclohexane (d) 1,4-Dichlorocyclohexaarrow_forwardWhat is the most stable chair conformation form of trans 1 -tert-butyl -3-methylcyclohexane? a)Axial tert-butyl, equatorial methyl b)Axial tert-butyl,equatorial methyl c)equatorial tert-butyl, equatorial methyl d)equatorial tert-butyl, Axial methylarrow_forward
- 1. Write the two chair conformations of each of the following and in each part designate which conformation would be the more stable:a. cis-1-tert-butyl-3-methylcyclohexaneb. trans-1-tert-butyl-3-methylcyclohexane 2. Construct a qualitative potential-energy diagram for rotation about the C–C bond of 1,2-dibromoethane. Which conformation would you expect to be most stable? Label the anti and gauche conformations of 1,2-dibromoethane.arrow_forward3 1. construct an energy diagram to show the variation in the free energy of the molecule as the front atom is rotated clockwise from 0 degrees to 360 degrees in 60 degrees increments. in your energy diagram you should clearly show the relative energies of each conformer 2. draw newman projections for each conformation in the bottom of your diagramarrow_forwardWhich of the described conformations of trans-1-isopropyl-3-methylcyclohexane will be the most stable? Select one: a. The one in which both groups are equatorial b. The one in which the isopropyl group is axial and methyl group is equatorial c. The one in which the twist boat conformation is adopted d. The one in which the methyl group is axial and the isopropyl group is equatorial e. The one in which two substituents (groups) are axialarrow_forward
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