Calculate the total strain energy in each of the two chair conformations of cis-1-tert-butyl-4-chlorocyclohexane. By how much energy is the more stable conformation favored (thi is the difference in energy between the two conformations)? NOTE: The strain energy for one H,Cl interaction is 1.0 kj/mol while for H,-C(CH3)3 (t-butyl) is 11.4 kJ/mol. H3C. H3C- CH3. CH2 Ring-flip H3C H3C H- A (A) A=1.0 kl/mol; B=11.4 kJ/mol; difference = 10.4 kJ/mol (B) A=2.0 kj/mol; B=22.8 kj/mol; difference 20.8 kJ/mol (C) A=3.0 k/mol; B=22.8 kj/mol; difference = 19.8 kJ/mol (D) A=1.0 kl/mol; B=22.8 k/mol; difference = 21.8 kJ/mol (E) A=2.0 k/mol; B=11.4 k/mol; difference = 9.4 kJ/mol

Calculate the total strain energy in each of the two chair conformations of cis-1-tert-butyl-4-chlorocyclohexane. By how much energy is the more stable conformation favored (thi is the difference in energy between the two conformations)? NOTE: The strain energy for one H,Cl interaction is 1.0 kj/mol while for H,-C(CH3)3 (t-butyl) is 11.4 kJ/mol. H3C. H3C- CH3. CH2 Ring-flip H3C H3C H- A (A) A=1.0 kl/mol; B=11.4 kJ/mol; difference = 10.4 kJ/mol (B) A=2.0 kj/mol; B=22.8 kj/mol; difference 20.8 kJ/mol (C) A=3.0 k/mol; B=22.8 kj/mol; difference = 19.8 kJ/mol (D) A=1.0 kl/mol; B=22.8 k/mol; difference = 21.8 kJ/mol (E) A=2.0 k/mol; B=11.4 k/mol; difference = 9.4 kJ/mol

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter2: Alkanes And Cycloalkanes

Section: Chapter Questions

Problem 2.46P

See similar textbooks

Similar questions

Consider 1-bromo-2-methylpropane and draw the following. (a) The staggered conformation(s) of lowest energy (b) The staggered conformation(s) of highest energy
The energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).
One of the chair conformations of cis-1-chloro-3-methylcyclohexane is more stable than the other by 15.5 kJ/mol. Use this, and the table below, to estimate the energy cost of a 1,3-diaxial interaction between a chlorine atom and a methyl group. 1,3-Diaxial Strain Energies for Monosubstituted Cyclohexanes kJ/mol Substituent Substituent kJ/mol -NH2 -CN, cyano 0.4 2.95 -F 0.5 -COOH 2.95 -C=CH, ethynyl 0.85 -CH=CH2 3.55 -CH3 -I 0.95 3.64 -CH2CH3 -Cl 3.65 1.1 -CH(CH3)2 1.2 4.5 -Br -C(CH3)3 10.5 -ОН 1.95 -CGH5 6.3 (Round your answer to one decimal place.) kJ/mol
Hello, I was reading an answer from the book Organic Chemistry by Brown et al. The question is 2.51 "Draw alternative chair conformations for each substituted cyclohexane and state which chair is more stable." There are then 4 cyclohexanes (labeled a-d). For the "a" cyclohexane, the substituents are arranged as a combination of axial and equatorial in both chair conformations. However, for the "b," "c," and "d," cyclohexanes one chair has only equatorial substituents, and the other chair has only axial substituents. Why is the "a" chair conformation different? https://www.bartleby.com/solution-answer/chapter-2-problem-251p-organic-chemistry-8th-edition/9781305580350/draw-alternative-chair-conformations-for-each-substituted-cyclohexane-and-state-which-chair-is-more/4532cd91-c341-11e9-8385-02ee952b546e
Consider 1-bromopropane, CH3CH2CH2Br. (a) Which of these is the lowest energy conformation?
Which of the following cyclohexane conformation is (are) consider to be the most stable conformation for cis-1,2-dimethylhexane? I II III
Given cyclohexane in a chair conformation, construct the more stable conformation of cis‑1‑methyl‑2‑propylcyclohexane by filling in the missing atoms or groups. Use the numbering provided on the ring.
The overall process of converting one chair conformation to another chair conformation is known as RING INVERSION or ring flipping and is a very rapid process. The cyclohexane ring inverts approximately 10 time a second at room temperature. Show this interconversion by drawing the two chair conformations and putting a reversible arrow between them to indicate a dynamic equilibrium. If we have a methylcyclohexane molecule and this undergoes ring inversion, whatwill be the resulting structure? ?
Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq. The table of "Axial Strain Energies for Monosubstituted Cyclohexanes" found in the "Strain Energy Increments" section of the Reference tool is useful for answering this question. CHO (CH₂)₂CH Group a is Group bis Group cis Submit Answer 8 8 8 Retry Entire Group 8 more group attempts remaining
Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq. The table of "Axial Strain Energies for Monosubstituted Cyclohexanes" found in the "Strain Energy Increments" section of the Reference tool is useful for answering this question. Br Group a is Group b is Group c is Br
[Review Topics] Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq. The table of "Axial Strain Energies for Monosubstituted Cyclohexanes" found in the "Strain Energy Increments" section of the Reference tool is useful for answering this question. CO₂H Hil... Group a is Group b is Group c is Submit Answer b [References] CH3 Retry Entire Group 8 more group attempts remaining
Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq. The table of "Axial Strain Energies for Monosubstituted Cyclohexanes" found in the "Strain Energy Increments" section of the Reference tool is useful for answering this question. H CI C Group a is Group b is Group c is a axial equatorial ax/eq CH₂CH3 b