Gibbs free energy differences between axial-substituted and equatorial-substituted chair conformations of cyclohexane were given in Table 2.4.Q. Calculate the ratio of equatorial to axial tert-butylcyclohexane at 25°C. Table 2.4 AG° (Axial-Equatorial) for Monosubstituted Cyclohexanes at 25°Caxial → equatorial-AG-AGGroupkJ/molkcal/molGroupkJ/molkcal/molC=N0.80.19NH,5.91.41F1.00.24СООН5.91.41C=CH1.70.41C=CH,7.11.701.90.45CH,7.281.74CI0.53CH,CH,CH(CH,),2.27.31.75Br2.40.579.02.15OH3.90.93C(CH,),21.05.00

The tert-butyl cyclohexane can occupy either axial or equatorial position. But due to its bulkiness,…

Table 2.4 AG° (Axial-Equatorial) for Monosubstituted Cyclohexanes at 25°C axial → equatorial -AG -AG Group kJ/mol kcal/mol Group kJ/mol kcal/mol C=N 0.8 0.19 NH, 5.9 1.41 F 1.0 0.24 СООН 5.9 1.41 C=CH 1.7 0.41 C=CH, 7.1 1.70 1.9 0.45 CH, 7.28 1.74 CI 0.53 CH,CH, CH(CH,), 2.2 7.3 1.75 Br 2.4 0.57 9.0 2.15 OH 3.9 0.93 C(CH,), 21.0 5.00

Table 2.4 AG° (Axial-Equatorial) for Monosubstituted Cyclohexanes at 25°C axial → equatorial -AG -AG Group kJ/mol kcal/mol Group kJ/mol kcal/mol C=N 0.8 0.19 NH, 5.9 1.41 F 1.0 0.24 СООН 5.9 1.41 C=CH 1.7 0.41 C=CH, 7.1 1.70 1.9 0.45 CH, 7.28 1.74 CI 0.53 CH,CH, CH(CH,), 2.2 7.3 1.75 Br 2.4 0.57 9.0 2.15 OH 3.9 0.93 C(CH,), 21.0 5.00

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry

Section4.SE: Something Extra

Problem 40AP: From the data in Figure 4-12 and Table 4-1, estimate the percentages of molecules that have their...

See similar textbooks

Related questions

Q: 13 Draw the molecule trans-1-ethyl-3- isopropylcyclohexane in its chair and its flipped chair…

A: The given molecule is 1-ethyl-3-isopropylcyclohexane. Ethyl group is -CH2CH3 and isopropyl group is…

Q: Which of the following is an incorrect statement: O somers have the same molecular formula such as…

A: Option A is coorect Because for structural isomerism molecular formula and molecular mass should be…

Q: Draw two different chair conformations of bromocyclohexane, showing all hydrogen atoms. identify…

Q: Construct the chair structures with the molecular models for trans-1-ethyl-3-methylcyclohexane. Find…

Q: Perspective drawings of Chair and Boat Conformers fo Cyclohexane (C6H12). Note it is impossible to…

A: Perspective drawings of Chair and Boat Conformers for Cyclohexane (C6H12) If the six carbon atoms of…

Q: Cyclohexane derivatives exist primarily in the most stable of the available chair conformations.…

A: Explanation - A conformation in which both substituents are equatorial will always be more stable…

Q: Draw Newman projections, in order of decreasing energy, for all staggered conformations of 1,2-…

Q: Draw and name the six isomeric cyclopentane of molecular formula C7H14. These will include four…

A: The isomers are as shown below: There are 4 constitutional isomers of cyclopentane with the same…

Q: Cyclohexane structures can have two chair conformations. Draw the alternate conformation of the…

A: In this question, we will draw the chair flip structure for the given compound.The name of given…

Q: 5. Draw the two chair conformations ("ring flips") of trans –1-ethyl-4-methylcyclohexane to show the…

Q: CH, H H CH, trans-1,2-Dimethylcyclohexane H CH, H. ČH, trans-1,3-Dimethyleyclohexane CH, H,C H…

A: Given structures,

Q: Which is more stable: cis- or trans-1-(1-ethylpropyl)-3-methylcyclohexane? Draw the most stable…

A: cis and trans conformer of substituted cyclohexane exist as boat conformer where the two bulky group…

Q: Perform a conformational analysis of 1,2-dibromo-1-fluoroethane, BrFCH-CH2Br. Pay attention to the…

A: 1,2-dibromo-1-fluoroethane i.e, FCHBrCH2Br

Q: 11. s) Draw the most stable conformation of 1,3-dichloro-2,4-difluorocyclohexane: 12. Which of the…

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

Q: 4.) For each of the following pairs, give the relationship between the two compounds. You many…

A: Hello. Since your question has multiple sub-parts, the first three sub-parts shall only be solved in…

Q: Is there a difference in the stability of the two cyclohexane conformations?

A: The structure of chemical compound can be represented as structural formula. A structural formula…

Q: (B) Draw two chair conformations of the following substituted cyclohexane and identify the most…

A: In chair conformation of cyclohexane the bulkier group (ethyl) is present at equatorial position It…

Q: From studies of the dipole moment of 1,2-dichloroethane in the gas phase at room temperature (25°C),…

A: Given data: Using the dipole moment studies of 1,2-dichloroethane, the ratio of molecules in the…

Q: Draw six isomeric cyclopentanes of molecular formula C7H14. These will include four constitutional…

A: Constitutional isomers: They have same molecular formula but different connectivity of atoms or…

Q: True or False: 1. The eclipsed conformation of a linear alkane IS called cis, while the anti…

Q: H H CH3 H H CH 宜

A: Stability

Q: Draw the most stable conformation of 1-chloro-3-isopropylcyclohexane and give its complete IUPAC…

A: The structure of 1-chloro-3-isopropylcyclohexane is as follows:

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

Gibbs free energy differences between axial-substituted and equatorial-substituted chair conformations of cyclohexane were given in Table 2.4.

Q. Calculate the ratio of equatorial to axial tert-butylcyclohexane at 25°C.

Table 2.4 AG° (Axial-Equatorial) for Monosubstituted Cyclohexanes at 25°C
axial → equatorial
-AG
-AG
Group
kJ/mol
kcal/mol
Group
kJ/mol
kcal/mol
C=N
0.8
0.19
NH,
5.9
1.41
F
1.0
0.24
СООН
5.9
1.41
C=CH
1.7
0.41
C=CH,
7.1
1.70
1.9
0.45
CH,
7.28
1.74
CI
0.53
CH,CH,
CH(CH,),
2.2
7.3
1.75
Br
2.4
0.57
9.0
2.15
OH
3.9
0.93
C(CH,),
21.0
5.00

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

Step 3

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 3 steps with 4 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

Numbering the main chain of branched alkanes For each organic compound in the table below, enter the locant of the highlighted side chain. compound CH₁₂ CH3 - CH, | C - CH₁₂ | - CH2-CH- CH3 CH3 - locant of highlighted side chain ☐ CH3 | CH3 CH2 | CH₁₂ C-CH2-CH CH3 - CH - CH3 ㅁ CH₁₂ CH2 CH3 བos ད ་ CH3-CH2- - C CH3 - CH3 ☐ 00. Ar
(a) (b) 1. CH3MgBr 2. H3O+ H3C OH I H3C-C-C-CH3 H3C H ОН H CH3 CH3 H3C CH3 H3C H₂SO4 C=C
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.
What are the hybridized bonds and bond type of the molecules in this reaction? propan-1-ol → propene + water C₃H₈O (l) → C3H6 (g) + H2O (l)
Using the average bond strengths below, estimate the molar heat of hydrogenation, AHhydrogenation, for the conversion of C4H6 to C4H10. CH₂=CH-CH=CH₂(g) + 2H₂(g) →→→ CH₂CH₂CH₂CH₂(g) || Bond C-H C=C H-H C-C kJ Bond Strength (kJ/mol) 413 614 436 348
8
An unknown compound of molecular formula C5H10O2, gives the HNMR data shown below. Which of the following structures is consistent with the data?
From the data in Figure 4-12 and Table 4-1, estimate the percentages of molecules that have their substituents in an axial orientation for the following compounds: (a) Isopropylcyclohexane (b) Fluorocyclohexane (c) Cyclohexanecarbonitrile, C6H11CN
A 1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group axial and one group equatorial. Explain.
I do not understand how to figure out the correct names for these compounds with substituded hydrocarbons.
Match the following organic compounds with their correct pair.
Here is the chemical structure of 2-bromobutane: Н Η Н Н HHHH C C- C C-H H :Br Η Н .. Decide whether each molecule in the table below is another molecule of 2-bromobutane, a molecule of an isomer of 2-bromobutane, or a molecule of an entirely different compound. molecule CH₂ CH₂-CH₂-CH-Br CH₂ CH₂ -CH₂ Br HI H H H Η H_ H-C- C-C- H-C-H H H relationship to 2-bromobutane (Choose one) (Choose one) Br: a molecule of an isomer of 2-bromobutane ▼