The position of the three hydroxyl groups present in cholic acid are to be located and whether they are axial or equatorial are to be identified. Further whether cholic acid is a A-B trans or a A-B cis steroid is to be stated. Concept introduction: If the two cyclohexane rings are fused in trans manner the two hydrogens at the ring junction will be diaxial. If the ring fusion is cis , then hydrogen at one ring junction is axial while that in the other junction is equatorial. Among the disubstituted cyclohexanes, 1,2- cis , 1,3- trans and 1,4- cis substituents will have axial and equatorial arrangements. 1,2- trans , 1,3- cis and 1,4- trans substituents will have either diequatorial or diaxial arrangements. To locate: The position of the three hydroxyl groups present in cholic acid. To identify: Whether they are axial or equatorial. To state: Whether cholic acid is A-B trans or a A-B cis steroid.

Question

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Answer 1

Question

Chapter 27.SE, Problem 11VC

Interpretation Introduction

Interpretation:

The position of the three hydroxyl groups present in cholic acid are to be located and whether they are axial or equatorial are to be identified. Further whether cholic acid is a A-B trans or a A-B cis steroid is to be stated.

Concept introduction:

If the two cyclohexane rings are fused in trans manner the two hydrogens at the ring junction will be diaxial. If the ring fusion is cis, then hydrogen at one ring junction is axial while that in the other junction is equatorial.

Among the disubstituted cyclohexanes, 1,2-cis, 1,3-trans and 1,4-cis substituents will have axial and equatorial arrangements. 1,2-trans, 1,3-cis and 1,4-trans substituents will have either diequatorial or diaxial arrangements.

To locate:

The position of the three hydroxyl groups present in cholic acid.

To identify:

Whether they are axial or equatorial.

To state:

Whether cholic acid is A-B trans or a A-B cis steroid.

Expert Solution & Answer

Answer to Problem 11VC

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Explanation of Solution

The structure of cholic acid represented by the model is

Organic Chemistry - With Access (Custom), Chapter 27.SE, Problem 11VC

Since lithocholic acid has the rings A and B fused in cis manner, the methyl group on C₉ has to be equatorial and the H C₁₀ has to be axial for ring A. In lithocholic acid, the -OH on C₃ (in ring A), is in 1,4 trans relationship with the methyl on C₉. Hence the â€“OH on C₃ occupies the equatorial position.

For ring B the methyl group on C₉ is axial and the H C₁₀ is equatorial. The OH group on C6 has 1,4 trans relationship with methyl on C₉ it has to occupy the axial position.

The rings C and D are trans fused. The methyl on C₁₃ and H on C₁₄ has diaxial arrangement. Since the OH group on C₁₂ has 1,2 trans relationship with methyl on C₁₃ it has to occupy the axial position.

The H on C₇ is axial for ring C. Since the OH group on C₁₂ is three carbons away from C₇ it has to occupy the axial position.

Conclusion

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

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Provide the reasonable steps to achieve the following synthesis.

Answer 2

Question

Chapter 27.SE, Problem 11VC

Interpretation Introduction

Interpretation:

The position of the three hydroxyl groups present in cholic acid are to be located and whether they are axial or equatorial are to be identified. Further whether cholic acid is a A-B trans or a A-B cis steroid is to be stated.

Concept introduction:

If the two cyclohexane rings are fused in trans manner the two hydrogens at the ring junction will be diaxial. If the ring fusion is cis, then hydrogen at one ring junction is axial while that in the other junction is equatorial.

Among the disubstituted cyclohexanes, 1,2-cis, 1,3-trans and 1,4-cis substituents will have axial and equatorial arrangements. 1,2-trans, 1,3-cis and 1,4-trans substituents will have either diequatorial or diaxial arrangements.

To locate:

The position of the three hydroxyl groups present in cholic acid.

To identify:

Whether they are axial or equatorial.

To state:

Whether cholic acid is A-B trans or a A-B cis steroid.

Expert Solution & Answer

Answer to Problem 11VC

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Explanation of Solution

The structure of cholic acid represented by the model is

Organic Chemistry - With Access (Custom), Chapter 27.SE, Problem 11VC

Since lithocholic acid has the rings A and B fused in cis manner, the methyl group on C₉ has to be equatorial and the H C₁₀ has to be axial for ring A. In lithocholic acid, the -OH on C₃ (in ring A), is in 1,4 trans relationship with the methyl on C₉. Hence the â€“OH on C₃ occupies the equatorial position.

For ring B the methyl group on C₉ is axial and the H C₁₀ is equatorial. The OH group on C6 has 1,4 trans relationship with methyl on C₉ it has to occupy the axial position.

The rings C and D are trans fused. The methyl on C₁₃ and H on C₁₄ has diaxial arrangement. Since the OH group on C₁₂ has 1,2 trans relationship with methyl on C₁₃ it has to occupy the axial position.

The H on C₇ is axial for ring C. Since the OH group on C₁₂ is three carbons away from C₇ it has to occupy the axial position.

Conclusion

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

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Answer 3

Question

Chapter 27.SE, Problem 11VC

Interpretation Introduction

Interpretation:

The position of the three hydroxyl groups present in cholic acid are to be located and whether they are axial or equatorial are to be identified. Further whether cholic acid is a A-B trans or a A-B cis steroid is to be stated.

Concept introduction:

If the two cyclohexane rings are fused in trans manner the two hydrogens at the ring junction will be diaxial. If the ring fusion is cis, then hydrogen at one ring junction is axial while that in the other junction is equatorial.

Among the disubstituted cyclohexanes, 1,2-cis, 1,3-trans and 1,4-cis substituents will have axial and equatorial arrangements. 1,2-trans, 1,3-cis and 1,4-trans substituents will have either diequatorial or diaxial arrangements.

To locate:

The position of the three hydroxyl groups present in cholic acid.

To identify:

Whether they are axial or equatorial.

To state:

Whether cholic acid is A-B trans or a A-B cis steroid.

Expert Solution & Answer

Answer to Problem 11VC

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Explanation of Solution

The structure of cholic acid represented by the model is

Organic Chemistry - With Access (Custom), Chapter 27.SE, Problem 11VC

Since lithocholic acid has the rings A and B fused in cis manner, the methyl group on C₉ has to be equatorial and the H C₁₀ has to be axial for ring A. In lithocholic acid, the -OH on C₃ (in ring A), is in 1,4 trans relationship with the methyl on C₉. Hence the â€“OH on C₃ occupies the equatorial position.

For ring B the methyl group on C₉ is axial and the H C₁₀ is equatorial. The OH group on C6 has 1,4 trans relationship with methyl on C₉ it has to occupy the axial position.

The rings C and D are trans fused. The methyl on C₁₃ and H on C₁₄ has diaxial arrangement. Since the OH group on C₁₂ has 1,2 trans relationship with methyl on C₁₃ it has to occupy the axial position.

The H on C₇ is axial for ring C. Since the OH group on C₁₂ is three carbons away from C₇ it has to occupy the axial position.

Conclusion

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

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Answer 4

Question

Chapter 27.SE, Problem 11VC

Interpretation Introduction

Interpretation:

The position of the three hydroxyl groups present in cholic acid are to be located and whether they are axial or equatorial are to be identified. Further whether cholic acid is a A-B trans or a A-B cis steroid is to be stated.

Concept introduction:

If the two cyclohexane rings are fused in trans manner the two hydrogens at the ring junction will be diaxial. If the ring fusion is cis, then hydrogen at one ring junction is axial while that in the other junction is equatorial.

Among the disubstituted cyclohexanes, 1,2-cis, 1,3-trans and 1,4-cis substituents will have axial and equatorial arrangements. 1,2-trans, 1,3-cis and 1,4-trans substituents will have either diequatorial or diaxial arrangements.

To locate:

The position of the three hydroxyl groups present in cholic acid.

To identify:

Whether they are axial or equatorial.

To state:

Whether cholic acid is A-B trans or a A-B cis steroid.

Expert Solution & Answer

Answer to Problem 11VC

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Explanation of Solution

The structure of cholic acid represented by the model is

Organic Chemistry - With Access (Custom), Chapter 27.SE, Problem 11VC

Since lithocholic acid has the rings A and B fused in cis manner, the methyl group on C₉ has to be equatorial and the H C₁₀ has to be axial for ring A. In lithocholic acid, the -OH on C₃ (in ring A), is in 1,4 trans relationship with the methyl on C₉. Hence the â€“OH on C₃ occupies the equatorial position.

For ring B the methyl group on C₉ is axial and the H C₁₀ is equatorial. The OH group on C6 has 1,4 trans relationship with methyl on C₉ it has to occupy the axial position.

The rings C and D are trans fused. The methyl on C₁₃ and H on C₁₄ has diaxial arrangement. Since the OH group on C₁₂ has 1,2 trans relationship with methyl on C₁₃ it has to occupy the axial position.

The H on C₇ is axial for ring C. Since the OH group on C₁₂ is three carbons away from C₇ it has to occupy the axial position.

Conclusion

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

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Answer 5

Chapter 27.SE, Problem 11VC

Interpretation Introduction

Interpretation:

The position of the three hydroxyl groups present in cholic acid are to be located and whether they are axial or equatorial are to be identified. Further whether cholic acid is a A-B trans or a A-B cis steroid is to be stated.

Concept introduction:

If the two cyclohexane rings are fused in trans manner the two hydrogens at the ring junction will be diaxial. If the ring fusion is cis, then hydrogen at one ring junction is axial while that in the other junction is equatorial.

Among the disubstituted cyclohexanes, 1,2-cis, 1,3-trans and 1,4-cis substituents will have axial and equatorial arrangements. 1,2-trans, 1,3-cis and 1,4-trans substituents will have either diequatorial or diaxial arrangements.

To locate:

The position of the three hydroxyl groups present in cholic acid.

To identify:

Whether they are axial or equatorial.

To state:

Whether cholic acid is A-B trans or a A-B cis steroid.

Expert Solution & Answer

Answer to Problem 11VC

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Explanation of Solution

The structure of cholic acid represented by the model is

Organic Chemistry - With Access (Custom), Chapter 27.SE, Problem 11VC

Since lithocholic acid has the rings A and B fused in cis manner, the methyl group on C₉ has to be equatorial and the H C₁₀ has to be axial for ring A. In lithocholic acid, the -OH on C₃ (in ring A), is in 1,4 trans relationship with the methyl on C₉. Hence the â€“OH on C₃ occupies the equatorial position.

For ring B the methyl group on C₉ is axial and the H C₁₀ is equatorial. The OH group on C6 has 1,4 trans relationship with methyl on C₉ it has to occupy the axial position.

The rings C and D are trans fused. The methyl on C₁₃ and H on C₁₄ has diaxial arrangement. Since the OH group on C₁₂ has 1,2 trans relationship with methyl on C₁₃ it has to occupy the axial position.

The H on C₇ is axial for ring C. Since the OH group on C₁₂ is three carbons away from C₇ it has to occupy the axial position.

Conclusion

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Answer 6

Chapter 27.SE, Problem 11VC

Interpretation Introduction

Interpretation:

The position of the three hydroxyl groups present in cholic acid are to be located and whether they are axial or equatorial are to be identified. Further whether cholic acid is a A-B trans or a A-B cis steroid is to be stated.

Concept introduction:

If the two cyclohexane rings are fused in trans manner the two hydrogens at the ring junction will be diaxial. If the ring fusion is cis, then hydrogen at one ring junction is axial while that in the other junction is equatorial.

Among the disubstituted cyclohexanes, 1,2-cis, 1,3-trans and 1,4-cis substituents will have axial and equatorial arrangements. 1,2-trans, 1,3-cis and 1,4-trans substituents will have either diequatorial or diaxial arrangements.

To locate:

The position of the three hydroxyl groups present in cholic acid.

To identify:

Whether they are axial or equatorial.

To state:

Whether cholic acid is A-B trans or a A-B cis steroid.

Expert Solution & Answer

Answer to Problem 11VC

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Explanation of Solution

The structure of cholic acid represented by the model is

Organic Chemistry - With Access (Custom), Chapter 27.SE, Problem 11VC

Since lithocholic acid has the rings A and B fused in cis manner, the methyl group on C₉ has to be equatorial and the H C₁₀ has to be axial for ring A. In lithocholic acid, the -OH on C₃ (in ring A), is in 1,4 trans relationship with the methyl on C₉. Hence the â€“OH on C₃ occupies the equatorial position.

For ring B the methyl group on C₉ is axial and the H C₁₀ is equatorial. The OH group on C6 has 1,4 trans relationship with methyl on C₉ it has to occupy the axial position.

The rings C and D are trans fused. The methyl on C₁₃ and H on C₁₄ has diaxial arrangement. Since the OH group on C₁₂ has 1,2 trans relationship with methyl on C₁₃ it has to occupy the axial position.

The H on C₇ is axial for ring C. Since the OH group on C₁₂ is three carbons away from C₇ it has to occupy the axial position.

Conclusion

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Answer 7

Chapter 27.SE, Problem 11VC

Interpretation Introduction

Interpretation:

The position of the three hydroxyl groups present in cholic acid are to be located and whether they are axial or equatorial are to be identified. Further whether cholic acid is a A-B trans or a A-B cis steroid is to be stated.

Concept introduction:

If the two cyclohexane rings are fused in trans manner the two hydrogens at the ring junction will be diaxial. If the ring fusion is cis, then hydrogen at one ring junction is axial while that in the other junction is equatorial.

Among the disubstituted cyclohexanes, 1,2-cis, 1,3-trans and 1,4-cis substituents will have axial and equatorial arrangements. 1,2-trans, 1,3-cis and 1,4-trans substituents will have either diequatorial or diaxial arrangements.

To locate:

The position of the three hydroxyl groups present in cholic acid.

To identify:

Whether they are axial or equatorial.

To state:

Whether cholic acid is A-B trans or a A-B cis steroid.

Answer 8

Expert Solution & Answer

Answer to Problem 11VC

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Answer 9

Expert Solution & Answer

Answer 10

Expert Solution & Answer

Answer 11

Explanation of Solution

The structure of cholic acid represented by the model is

Organic Chemistry - With Access (Custom), Chapter 27.SE, Problem 11VC

Since lithocholic acid has the rings A and B fused in cis manner, the methyl group on C₉ has to be equatorial and the H C₁₀ has to be axial for ring A. In lithocholic acid, the -OH on C₃ (in ring A), is in 1,4 trans relationship with the methyl on C₉. Hence the â€“OH on C₃ occupies the equatorial position.

For ring B the methyl group on C₉ is axial and the H C₁₀ is equatorial. The OH group on C6 has 1,4 trans relationship with methyl on C₉ it has to occupy the axial position.

The rings C and D are trans fused. The methyl on C₁₃ and H on C₁₄ has diaxial arrangement. Since the OH group on C₁₂ has 1,2 trans relationship with methyl on C₁₃ it has to occupy the axial position.

The H on C₇ is axial for ring C. Since the OH group on C₁₂ is three carbons away from C₇ it has to occupy the axial position.

Answer 12

Conclusion

The three hydroxyl groups are on C₃, C₆ and C₁₂. The hydroxyl group on C₃ is equatorial while those at C₆ and C₁₂ are axial. Cholic acid is A-B cis steroid.

Answer 13

Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3P Ch. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5P Ch. 27.5 - Prob. 6P Ch. 27.5 - Prob. 7P Ch. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an Aâ€“B cis steroid found in...Ch. 27.7 - Prob. 10P

Answer to Problem 11VC

Explanation of Solution

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Chapter 27 Solutions