Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 3.9, Problem 33P
- a. Draw the most stable conformation of pentane for rotation about the C-2―C-3 bond.
- b. Draw the least stable conformation of pentane for rotation about the C-2―C-3 bond.
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Consider pentane, C5H12. Looking through the internal C3-C4single bond, draw thesix Newman projections (where the angle between two bonds as you look through the C3and C4bond is either 0°or 60°of the different conformations. Label the conformers/rotamers using I, II, etc.
a.Which conformer is the most stable? the least stable?
b.Which rotamer is the anticonformer? the gaucheconformer?
c.Draw the anticonformer in saw horse projection.
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?
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?
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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- Which is the most stable conformation for propane? refer to 5.jpgarrow_forwardWhich 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_forwardrotation here a. Draw the three staggered and three eclipsed conformations that result from rotation around the designated bond using Newman projections. b. Label the most stable and least stable conformation. CH3-C-CH,CH3arrow_forward
- H₂C. CH3 CH3 CH₂ + + O H₂C=CHCCH3 EN heat heatarrow_forward1. Draw the two conformations of trans-1-bromo-3-methylcyclohexane using both the Newman projection and the chair drawing. Calculate the energies of each. What ratio of the two conformers will be present at equilibrium? 2. Draw a structure of a chiral alcohol.arrow_forwarda. Draw the lowest energy conformation for the compound shown in the image. b. Draw the complete structural formula of the following compound: cis-1-bromo-3-chlorocyclohexane.arrow_forward
- Which 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_forward3. For each pair, predict which conformation is more stable and explain the physical reason for the difference in stability.arrow_forwardDraw clear pictures showing the two chair conformations of this compound. 1. Circle the lower energy (more stable) conformation or write "same energy".arrow_forward
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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License