ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 4, Problem 4.45P
Which conformation in each pair is higher in energy? Calculate the energy difference between the two conformations using the values given in Table 4.3.
a. 
b. 
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3. For each pair, predict which conformation is more stable and explain the physical reason
for the difference in stability.
There are the two possible chair conformations of trans-1-Methyl-4-chlorocyclohexane. What is the energy difference between the two chair conformations?
Table 1. Steric Strain in Monosubstituted Cyclohexanes
a 28
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d 9.6
Ethane spends all its time in the staggered conformation because it has the lowest potential energy.
a. True
b. False
c. Neither
Chapter 4 Solutions
ORGANIC CHEMISTRY
Ch. 4 - Prob. 4.1PCh. 4 - Problem 4.2 Which of the following is not another...Ch. 4 - Problem 4.3 Draw the five constitutional isomers...Ch. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Draw the five constitutional isomers that have...Ch. 4 - Problem 4.7 Give the IUPAC name for each...Ch. 4 - Give the IUPAC name for each compound. a....Ch. 4 - Problem 4.9 Give the structure corresponding to...Ch. 4 - Prob. 4.10P
Ch. 4 - Give the IUPAC name for each compound.Ch. 4 - Give the structure corresponding to each IUPAC...Ch. 4 - Arrange the following compounds in order of...Ch. 4 - Problem 4.14 Draw the staggered and eclipsed...Ch. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Problem 4.17 a. Draw the three staggered and...Ch. 4 - Problem 4.18 Rank the following conformations in...Ch. 4 - Problem 4.19 Consider rotation around the...Ch. 4 - Calculate the destabilization present in each...Ch. 4 - Problem 4.21 Classify the ring carbons as up or...Ch. 4 - Problem 4.22 Using the cyclohexane with the C’s...Ch. 4 - Draw a second chair conformation for each...Ch. 4 - Problem 4.24 Draw both conformations for and...Ch. 4 - Problem 4.25 Draw the structure for each compound...Ch. 4 - For cis-1, 3-diethylcyclobutane, draw a a...Ch. 4 - Prob. 4.27PCh. 4 - Problem 4.28 Consider .
Draw structures f or the...Ch. 4 - Problem 4.29 Draw a chair conformation of...Ch. 4 - Prob. 4.30PCh. 4 - Draw the products of each combustion reaction.Ch. 4 - Explain why beeswax is insoluble in H2O, slightly...Ch. 4 - Prob. 4.33PCh. 4 - Name each alkane using the ball-and-stick model,...Ch. 4 - Consider the substituted cyclohexane shown in the...Ch. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - 4.38 Give the IUPAC name for each compound.
a. c....Ch. 4 - 4.39 Give the structure and IUPAC name for each of...Ch. 4 -
4.40 Draw the structure corresponding to each...Ch. 4 - Prob. 4.41PCh. 4 - 4.42 Give the IUPAC name for each compound.
a....Ch. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - 4.45 Which conformation in each pair is higher in...Ch. 4 - 4.46 Considering rotation around the bond...Ch. 4 - Prob. 4.47PCh. 4 - 4.48 (a) Using Newman projections, draw all...Ch. 4 - 4.49 Label the sites of torsional and steric...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 - 4.56 Convert each of the following structures into...Ch. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - 4.59 Classify each pair of compounds as...Ch. 4 - Classify each pair of compounds as constitutional...Ch. 4 - Prob. 4.61PCh. 4 - 4.62 Draw the three constitutional isomers having...Ch. 4 - Prob. 4.63PCh. 4 - 4.64 Draw the products of combustion of each...Ch. 4 - 4.65 Hydrocarbons like benzene are metabolized in...Ch. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Cyclopropane and cyclobutane have similar strain...Ch. 4 - Prob. 4.69PCh. 4 - Haloethanes (CH3CH2X,X=Cl,Br,I) have similar...Ch. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 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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- Draw the two conformations and which is the most stablearrow_forwarda. Draw the three staggered and three eclipsed conformations that result from rotation around the bond labeled in red using Newman projections. b. Label the most stable and least stable conformation.arrow_forwarda.Draw the three staggered and three eclipsed conformations that result from rotation around the bond labeled in red using Newman projections. b. Label the most stable and least stable conformation.arrow_forward
- 2. Draw the flipped chair conformation of a. Which of the two conformations is more stable? Justify your answer. #s S.arrow_forwardneed all parts to get upvote need it sooonnarrow_forward5. For the pair of compounds circle the compound which is more stable (you may find it helpful to draw out the chair conformation)arrow_forward
- "The staggered conformations are more stable (lower in energy) than the eclipsed conformations" Explain this ?arrow_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_forwardConsider 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?arrow_forward
- 2. Draw the two chair conformations of menthol and identify the more stable conformation.arrow_forwardLook at the model of chloroethane. a) Do all chloroethane molecules spend all of their time in this preferred conformation? Explain why or why not. b) What is the preferred conformation called?arrow_forwardDraw the following molecules in their most stable conformation. You do not have to draw the least stable conformation, unless you find it helpful practice.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