(a) Interpretation: The energy difference between the two chair conformations of t r a n s − 1 , 4 − dimethylcylohexane is to be calculated. Concept introduction: The conformation of cyclohexane is a type of 3 − D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Question

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Answer 1

Question

Chapter 7, Problem 7.14P

Interpretation Introduction

(a)

Interpretation:

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is 14.8 kJ mol−1.

Explanation of Solution

The two chair conformations of trans−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 1

Figure 1

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation A of trans−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 2

Figure 2

Thus, there are total four 1,3−diaxial interactions between hydrogen and methyl present in the given compound.

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of four 1,3−diaxial interactions in energy is calculated as,

Energy contributed by four 1,3−diaxial interaction=4×3.7 kJ mol−1=14.8 kJ mol−1

In case of chair conformation B, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=14.8 kJ mol−1−0 kJ mol−1=14.8 kJ mol−1

Thus, the energy difference is 14.8 kJ mol−1.

Conclusion

The energy difference between the two chair conformations of the given compound is 14.8 kJ mol−1.

Interpretation Introduction

(b)

Interpretation:

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

Explanation of Solution

The chair conformations of cis−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 3

Figure 3

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation of cis−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 4

Figure 4

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of two 1,3−diaxial interactions in energy is calculated as,

Energy contributed by two 1,3−diaxial interaction=2×3.7 kJ mol−1=7.4 kJ mol−1

The most stable chair conformation of trans−1,4−dimethylcylohexane are shown below.

Figure 5

In case of most stable chair conformation of trans−1,4−dimethylcylohexane, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane and cis−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=7.4 kJ mol−1−0 kJ mol−1=7.4 kJ mol−1

Thus, the energy difference is 7.4 kJ mol−1.

Conclusion

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

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Answer 2

Question

Chapter 7, Problem 7.14P

Interpretation Introduction

(a)

Interpretation:

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is 14.8 kJ mol−1.

Explanation of Solution

The two chair conformations of trans−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 1

Figure 1

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation A of trans−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 2

Figure 2

Thus, there are total four 1,3−diaxial interactions between hydrogen and methyl present in the given compound.

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of four 1,3−diaxial interactions in energy is calculated as,

Energy contributed by four 1,3−diaxial interaction=4×3.7 kJ mol−1=14.8 kJ mol−1

In case of chair conformation B, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=14.8 kJ mol−1−0 kJ mol−1=14.8 kJ mol−1

Thus, the energy difference is 14.8 kJ mol−1.

Conclusion

The energy difference between the two chair conformations of the given compound is 14.8 kJ mol−1.

Interpretation Introduction

(b)

Interpretation:

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

Explanation of Solution

The chair conformations of cis−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 3

Figure 3

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation of cis−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 4

Figure 4

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of two 1,3−diaxial interactions in energy is calculated as,

Energy contributed by two 1,3−diaxial interaction=2×3.7 kJ mol−1=7.4 kJ mol−1

The most stable chair conformation of trans−1,4−dimethylcylohexane are shown below.

Figure 5

In case of most stable chair conformation of trans−1,4−dimethylcylohexane, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane and cis−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=7.4 kJ mol−1−0 kJ mol−1=7.4 kJ mol−1

Thus, the energy difference is 7.4 kJ mol−1.

Conclusion

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

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Answer 3

Question

Chapter 7, Problem 7.14P

Interpretation Introduction

(a)

Interpretation:

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is 14.8 kJ mol−1.

Explanation of Solution

The two chair conformations of trans−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 1

Figure 1

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation A of trans−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 2

Figure 2

Thus, there are total four 1,3−diaxial interactions between hydrogen and methyl present in the given compound.

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of four 1,3−diaxial interactions in energy is calculated as,

Energy contributed by four 1,3−diaxial interaction=4×3.7 kJ mol−1=14.8 kJ mol−1

In case of chair conformation B, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=14.8 kJ mol−1−0 kJ mol−1=14.8 kJ mol−1

Thus, the energy difference is 14.8 kJ mol−1.

Conclusion

The energy difference between the two chair conformations of the given compound is 14.8 kJ mol−1.

Interpretation Introduction

(b)

Interpretation:

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

Explanation of Solution

The chair conformations of cis−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 3

Figure 3

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation of cis−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 4

Figure 4

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of two 1,3−diaxial interactions in energy is calculated as,

Energy contributed by two 1,3−diaxial interaction=2×3.7 kJ mol−1=7.4 kJ mol−1

The most stable chair conformation of trans−1,4−dimethylcylohexane are shown below.

Figure 5

In case of most stable chair conformation of trans−1,4−dimethylcylohexane, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane and cis−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=7.4 kJ mol−1−0 kJ mol−1=7.4 kJ mol−1

Thus, the energy difference is 7.4 kJ mol−1.

Conclusion

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

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Answer 4

Question

Chapter 7, Problem 7.14P

Interpretation Introduction

(a)

Interpretation:

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is 14.8 kJ mol−1.

Explanation of Solution

The two chair conformations of trans−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 1

Figure 1

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation A of trans−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 2

Figure 2

Thus, there are total four 1,3−diaxial interactions between hydrogen and methyl present in the given compound.

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of four 1,3−diaxial interactions in energy is calculated as,

Energy contributed by four 1,3−diaxial interaction=4×3.7 kJ mol−1=14.8 kJ mol−1

In case of chair conformation B, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=14.8 kJ mol−1−0 kJ mol−1=14.8 kJ mol−1

Thus, the energy difference is 14.8 kJ mol−1.

Conclusion

The energy difference between the two chair conformations of the given compound is 14.8 kJ mol−1.

Interpretation Introduction

(b)

Interpretation:

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

Explanation of Solution

The chair conformations of cis−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 3

Figure 3

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation of cis−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 4

Figure 4

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of two 1,3−diaxial interactions in energy is calculated as,

Energy contributed by two 1,3−diaxial interaction=2×3.7 kJ mol−1=7.4 kJ mol−1

The most stable chair conformation of trans−1,4−dimethylcylohexane are shown below.

Figure 5

In case of most stable chair conformation of trans−1,4−dimethylcylohexane, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane and cis−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=7.4 kJ mol−1−0 kJ mol−1=7.4 kJ mol−1

Thus, the energy difference is 7.4 kJ mol−1.

Conclusion

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

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Answer 5

Chapter 7, Problem 7.14P

Interpretation Introduction

(a)

Interpretation:

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is 14.8 kJ mol−1.

Explanation of Solution

The two chair conformations of trans−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 1

Figure 1

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation A of trans−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 2

Figure 2

Thus, there are total four 1,3−diaxial interactions between hydrogen and methyl present in the given compound.

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of four 1,3−diaxial interactions in energy is calculated as,

Energy contributed by four 1,3−diaxial interaction=4×3.7 kJ mol−1=14.8 kJ mol−1

In case of chair conformation B, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=14.8 kJ mol−1−0 kJ mol−1=14.8 kJ mol−1

Thus, the energy difference is 14.8 kJ mol−1.

Conclusion

The energy difference between the two chair conformations of the given compound is 14.8 kJ mol−1.

Interpretation Introduction

(b)

Interpretation:

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

Explanation of Solution

The chair conformations of cis−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 3

Figure 3

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation of cis−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 4

Figure 4

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of two 1,3−diaxial interactions in energy is calculated as,

Energy contributed by two 1,3−diaxial interaction=2×3.7 kJ mol−1=7.4 kJ mol−1

The most stable chair conformation of trans−1,4−dimethylcylohexane are shown below.

Figure 5

In case of most stable chair conformation of trans−1,4−dimethylcylohexane, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane and cis−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=7.4 kJ mol−1−0 kJ mol−1=7.4 kJ mol−1

Thus, the energy difference is 7.4 kJ mol−1.

Conclusion

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

Answer 6

Chapter 7, Problem 7.14P

Interpretation Introduction

(a)

Interpretation:

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is 14.8 kJ mol−1.

Explanation of Solution

The two chair conformations of trans−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 1

Figure 1

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation A of trans−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 2

Figure 2

Thus, there are total four 1,3−diaxial interactions between hydrogen and methyl present in the given compound.

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of four 1,3−diaxial interactions in energy is calculated as,

Energy contributed by four 1,3−diaxial interaction=4×3.7 kJ mol−1=14.8 kJ mol−1

In case of chair conformation B, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=14.8 kJ mol−1−0 kJ mol−1=14.8 kJ mol−1

Thus, the energy difference is 14.8 kJ mol−1.

Conclusion

The energy difference between the two chair conformations of the given compound is 14.8 kJ mol−1.

Answer 7

Chapter 7, Problem 7.14P

Interpretation Introduction

(a)

Interpretation:

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Answer 8

Expert Solution

Answer to Problem 7.14P

The energy difference between the two chair conformations of trans−1,4−dimethylcylohexane is 14.8 kJ mol−1.

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The two chair conformations of trans−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 1

Figure 1

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation A of trans−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 2

Figure 2

Thus, there are total four 1,3−diaxial interactions between hydrogen and methyl present in the given compound.

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of four 1,3−diaxial interactions in energy is calculated as,

Energy contributed by four 1,3−diaxial interaction=4×3.7 kJ mol−1=14.8 kJ mol−1

In case of chair conformation B, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=14.8 kJ mol−1−0 kJ mol−1=14.8 kJ mol−1

Thus, the energy difference is 14.8 kJ mol−1.

Answer 13

Conclusion

The energy difference between the two chair conformations of the given compound is 14.8 kJ mol−1.

Answer 14

Interpretation Introduction

(b)

Interpretation:

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution

Answer to Problem 7.14P

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

Explanation of Solution

The chair conformations of cis−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 3

Figure 3

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation of cis−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 4

Figure 4

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of two 1,3−diaxial interactions in energy is calculated as,

Energy contributed by two 1,3−diaxial interaction=2×3.7 kJ mol−1=7.4 kJ mol−1

The most stable chair conformation of trans−1,4−dimethylcylohexane are shown below.

Figure 5

In case of most stable chair conformation of trans−1,4−dimethylcylohexane, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane and cis−1,4−dimethylcylohexane is calculated as,

Energy difference=Energy given by conformation A−Energy given by conformation B

Substitute the values of energies in above equation.

Energy difference=7.4 kJ mol−1−0 kJ mol−1=7.4 kJ mol−1

Thus, the energy difference is 7.4 kJ mol−1.

Conclusion

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

Answer 15

Interpretation Introduction

(b)

Interpretation:

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is to be calculated.

Concept introduction:

The conformation of cyclohexane is a type of 3−D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Answer 16

Expert Solution

Answer to Problem 7.14P

The energy difference between cis−1,4−dimethylcylohexane and the more stable conformation of trans−1,4−dimethylcylohexane is 7.4 kJ mol−1.

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The chair conformations of cis−1,4−dimethylcylohexane are shown below.

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 3

Figure 3

The 1,3−diaxial interaction between hydrogen and methyl present in the chair conformation of cis−1,4−dimethylcylohexane that is shown as,

ORGANIC CHEM +SG +SAPLING >IP<, Chapter 7, Problem 7.14P , additional homework tip 4

Figure 4

The given value of contribution one 1,3−diaxial interaction between hydrogen and methyl in energy is 3.7 kJ mol−1(0.9 kcal/mol). Therefore, the contribution of two 1,3−diaxial interactions in energy is calculated as,

Energy contributed by two 1,3−diaxial interaction=2×3.7 kJ mol−1=7.4 kJ mol−1

The most stable chair conformation of trans−1,4−dimethylcylohexane are shown below.

Figure 5

In case of most stable chair conformation of trans−1,4−dimethylcylohexane, there is no 1,3−diaxial interaction exists between hydrogen and methyl. Thus, its energy contribution is zero.

Therefore, the energy difference of between the two chair conformations of trans−1,4−dimethylcylohexane and cis−1,4−dimethylcylohexane is calculated as,