Given the structures of the following two tetramethylcyclohexanes: CH3 CH3 CH3 CH3 CH3 CH3 A В (a) Draw the most stable chair conformation for both A and B. Which structure is lower in energy (most stable)?

Given the structures of the following two tetramethylcyclohexanes: CH3 CH3 CH3 CH3 CH3 CH3 A В (a) Draw the most stable chair conformation for both A and B. Which structure is lower in energy (most stable)?

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

Section2.6: Cis,trans Isomerism In Cycloalkanes And Bicycloalkanes

Problem 2.13P: Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the...

See similar textbooks

Related questions

Q: 4. Draw the most and least stable conformations of the following substituted cyclohexanes in the…

A: For most stable chair conformation, the bulky group is attached to the equatorial position

Q: H3C)2HC "CH2CH

Q: Et Br Br Et

A: Applying chair from and 1,3 diaxial interaction interpretation.

Q: 2. For the following structure: (1S, 2R, 4R)-2-chloro-1-isopropyl-4-methylcyclohexane a. draw both…

Q: Draw the two chair conformations of each compound, and label the substituents as axial and…

A: The chair conformations are the accurate representation of cyclohexane rings that are actually…

Q: 3) Draw both chair conformations of (1S,3R)-1-chloro-3-isopropylcyclohexane. Clearly mark the most…

Q: 10. Rank the indicated conformations in order of decreasing stability (from L-R). CH₂ CH3 H CH, Н…

Q: Which of the following is the most stable conformation of cis-1-isopropyl-3-methylcyclohexane?…

A: “Since you have asked multiple questions, we will solve the first question for you. If you want any…

Q: Draw the two chair conformations of each compound, and label the substituents as axial and…

Q: Which conformer of butane is the lowest in energy? H3C CH3 H3C CH3 A C H H H H3C н H3C H •H H B D…

A: Since we know that anti form of butane is most stable and lowest energy conformer...

Q: 2.68 Draw the two chair conformations of menthol, and tell which is more stable. CH3 Menthol HO…

Q: 8. What is the correct order of stability, starting with the most strained, for the conformations…

Q: (1) Provide clear drawings of both chair conformations of trans-3(tert- butyl)cyclohexan-1-ol. (6)…

A: (i) Given compound named trans-3-(tert-butyl) cyclohexan-1-ol , have two substituents at cyclohexane…

Q: 8. Which of the following is the most stable conformation of trans-1-tert-butyl-3-…

A: Given compound: trans-1-tert-butyl-3-methylcyclohexane

Q: 5) For the following: a) Draw the "flat" line structure of the following (be sure to indicate…

A: Cyclohexane is most stable in the chair confirmation. Interconversion of confirmation of cyclohexane…

Q: Assign the absolute configuration of all molecules. Draw the most stable conformer in Newman…

Q: 11. Draw the Newman projection of the alkane conformation shown below looking down the indicated C-C…

A: Newman projection: These are one of the ways to explain stereochemistry of alkanes. The…

Q: Draw cis-1,2-dimethylcyclohexane in its more stable chair conformation. Are the methyl groups axial…

A: Cis-1,2-dimethylcyclohexane in its more stable chair conformation, In this given compound, one…

Q: 2. a) Draw the most stable chair confomation of: cis 1,3-dichlorocyciohexane b) Draw a Newman…

A: The structures of the organic compounds given are

Q: g. Draw two chair conformations of the following molecule and indicate which one is more stable. h.…

A: Here we have to write the chair conformation and predict the most stable conformation of the…

Q: 2. For each compound below, draw two chair conformations and identify which of them is more stable.…

Q: 9) Draw trans-1,3-dichloro cyclohexane in the highest energy conformation.

A: The increasing order of energy of conformer of cyclohexane are as follows: Chair<Twisted…

Q: 8. Predict the most stable conformation of each of the following molecules and explain the basis of…

Q: Question attached

A: An eclipse conformation infers that the substituents attached to two adjacent atoms are so close…

Q: Sighting along the appropriate C-C bond of neopentane C(CH3)4: a) Draw its Newman projections. b)…

Q: For the following compound, draw the appropriate Newman projection along the N2-C3 bond of the…

A: The compound given is . In the above compound we can see that on N, there is a H and CH3 group along…

Q: Which of the following is the most stable chair conformation of trans-1-bromo-2- methylcyclohexane?…

Q: 2. Draw the most stable conformation of the following: (a) trans-1-butyl-3-methylcyclohexane (b)…

A: Bulky group should be present at equitorial position for stability so that it can feel minimum…

Q: 2.32 A trisubstituted cyclohexane with three substituents-red, green, and blue-undergoes a ring-flip…

Q: 3.Draw the most stable chair conformation for each of the following compounds (a)…

A: Chair conformation of cyclohexane is more stable.

Q: Draw the Newman projections of 3-methylpentane looking down C2-C3 bond. Identify the most stable…

A: The compounds having same molecular formula, but they have dissimilar spatial arrangement of atoms…

Q: 4. Draw a chair conformation for the most stable isomer of 1,3,4-tri methylcyclchexane in its most…

A: cyclohexane compound is not planer, its real existence is chair form , in chair form notation for…

Q: Given the following geometric isomers: H H H A Br В ČH3 CH3 Br H What is the preferred chair…

A: in ring upper bond is wedge and lower bond is dash. for more stable cyclohexane bulky group is…

Q: 14. Which one iis the second possible chair conformation for the following compound. MoH HO B. C. D.…

A: Given Structure= Trans 1,3 dihydroxy Cyclohexane Other possible structure = ?

Q: Conformer E is a (cis/trans) isomer. A conformational ring flip of conformer E will yield conformer…

Q: 3.1 Draw both chair conformations of compound M on the templates (X and Y) provided. Indicate which…

A: Since you have asked multiple question we will solve the first one for you if you want answer to…

Q: See in attachment (a) Draw C in its more stable chair conformation. (b) Convert D to a hexagon with…

A: To find: The more stable chair conformer of C Conversion of D into hexagon

Q: ght along the C2-C3 blond of 2-methylbutane: a)draw the newman projection of the most stable…

Q: One of the chair conformers of cis-1,3-dimethylcyclohexane is 5.4 kcal/mol less stable than the…

A: solution- steric strain does a 1,3-diaxial interaction between two methyl groups introduce into the…

Q: Given the structures of the following two tetramethylcyclohexanes: CH3 CH3 CH3 "CH3 CH3 CH3 A В (a)…

Q: Menthol is a common additive to dental products, topical analgesics, decongestants and many other…

A: Menthol is a common additive to dental products, topical analgesics, decongestants and may other…

Q: The diaxial conformation of cis- 1,3-dimethylcyclohexane is approximately 23 kl/mol (5.4 kcal/mol)…

A: We have been asked to draw the chair conformation and show the unstability of diaxial conformation.

Q: ing is CH3 CH3 *** CH3 CH3 H3C H. CH3 H. H. H' H. H. ČH3 IV А) I B) II С) I D) IV 40. Which of the…

Q: Sighting down the Ci-C2 bond axis of 1-bromopentane, Br-CH2-CH÷CH»CH=CH®, draw the Newman projection…

A: Given that : For 1-bromopentane, we have to draw the Newman projection of : a) the anti staggered…

Q: Draw the most stable conformation of the disubstituted cyclohexane below

A: Conformational isomers: The conformational isomers are formed by the rotation of a carbon-carbon…

Q: Draw the two chair conformations of each compound, and label the substituents as axial and…

A: The two chair conformations of cis-1-ethyl-3-methylcyclohexane has to be drawn.

Q: Draw the two chair conformations of each compound, and label the substituents as axial and…

A: Chair conformation: These conformations are usually applicable for the cyclohexane compounds. The…

Q: 2. a) Draw the most stable chair conformation of cis 1-isobutyl-2-methylcyclohexane. b) Draw a…

Q: 6.26 Br Me Me Br

A: The conformer with bulkier group on equatorialis more stable than the conformer having bulkier group…

Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

Given the structures of the following two tetramethylcyclohexanes:
CH3
CH3
H3C"
CH3
H3C"
CH3
CH3
CH3
A
B
(a) Draw the most stable chair conformation for both A and B. Which structure is lower in energy
(most stable)?
(b) Ring flip the above structures and draw the least stable chair conformation for both A and B.
Which structure is highest in energy (least stable)?

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

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

Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the alternative chair conformations of this compound and state which of the two is more stable.
draw the most stable conformation of (a) ethylcyclohexane (b) 3-isopropyl-1,1-dimethylcyclohexane
H C-Ć- C -CI Following is the structural formula of 1,2– dichloroethane. H H a) Draw Newman projections for all staggered and eclipsed conformations formed by rotation from 0° to 360° about the carbon- carbon single bond. b) Which staggered conformation(s) has the lowest energy; which has the highest energy? c) Which eclipsed conformation(s) has the lowest energy which has the highest energy?
Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3- dimethylcyclohexane, and 1,4-dimethylcyclohexane. (a ) Indicate by a label whether each methyl group is axial or equatorial. (b) For which isomer(s) are the alternative chair conformations of equal stability? (c) For which isomer(s) is one chair conformation more stable than the other?
1E.) Which of the following two conformers is lower in energy? Both conformers are of equal enery O A Conformer A is lower in energy. B Conformer B is lower in energy. It cannot be determined
Sighting along the appropriate C-C bond of neopentane C(CH3)4: a) Draw its Newman projections. b) How much energy does the most unstable conformation possess? c) Make the energy diagram for the different conformers.
Consider the following chair conformation of bromocyclohexane: H H H Br H H H (a) Identify whether the bromine atom occupies an axial position or an equatorial position in the conformation above. (b) Draw a bond-line drawing (skeletal structure) of this chair conformation (without Newman projections). (c) Draw a bond-line drawing of the other chair conformation (after a ring flip).
5) For the following: a) Draw the "flat" line structure of the following (be sure to indicate stereochemistry) Br OH b) Draw both chair conformations of the following compound. Indicate which form is the most stable H3C°
Draw each compound in its most stable conformation(s). Then draw it in its most symmetric conformation, and determine whether it is chiral.(a) 2-methylbutane
Monosubstituted cyclohexanes occur in two equilibrium conformations. In one conformation, the substituent is in an axial position. In the other conformation, the substituent is in the equatorial position. Complete the drawing of each chair conformation below and circle the more stable conformation. Br
3. For the following conformation of 1,3-dimethylcyclohexane: H₂C. -CH3 A a) Is this a chair conformation of cis- or trans- isomer of 1,3-dimethylcyclohexane? b) Draw the alternative chair conformation of this compound. Which chair conformation is more stable? c) Draw a planar hexagon representation of the isomer A. d) Draw a Newman projection of isomer A.
Consider 1-bromopropane, CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?