(a) Interpretation: The stereogenic center at C15 is to be labeled as R or S . Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from 1 → 2 → 3 . The configuration of the compound is R and S when circle rotates in clockwise and anticlockwise direction.

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Answer 1

Question

Chapter 31, Problem 31.25P

Interpretation Introduction

(a)

Interpretation: The stereogenic center at C15 is to be labeled as R or S.

Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from 1→2→3. The configuration of the compound is R and S when circle rotates in clockwise and anticlockwise direction.

Interpretation Introduction

(b)

Interpretation: The two isomeric products formed on reaction of A with Zn(BH4)2 is to be drawn.

Concept introduction: Zincborohydride is a metal hydride reagent. It is a mild reducing agent which reduces ketones to alcohol. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The reagent used to convert the A to the single stereoisomer X is to be predicted.

Concept introduction: The chiral oxazaborolidine catalysts are enantiomeric selective reducing reagent. The carbonyl group of ketones are reduced to form one stereoisomer in the enantiomeric excess.

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A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired configuration. a. Label this stereogenic center as R or S. b. A well-known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship. d. Suggest a reagent to convert A to the single stereoisomer X.

A difficult problem in the synthesis of PGF2α is the introduction of the OH group at C15 in the desired conguration.a. Label this stereogenic center as R or S.b. A well known synthesis of PGF2α involves reaction of A with Zn(BH4)2, a metal hydride reagent similar in reactivity to NaBH4, to form two isomeric products, B and C. Draw their structures and indicate their stereochemical relationship.c. Suggest a reagent to convert A to the single stereoisomer X.

(R)-2-butanol reacts with phosphorus tribromide to give A (C4H9Br). Treatment of A with sodium cyanide in DMF gives B (C5H9)N. B is optically active. Draw the structure of B. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Show stereochemistry in a meso compound. Sn [F ? ChemDoodleⓇ

Answer 2

Question

Chapter 31, Problem 31.25P

Interpretation Introduction

(a)

Interpretation: The stereogenic center at C15 is to be labeled as R or S.

Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from 1→2→3. The configuration of the compound is R and S when circle rotates in clockwise and anticlockwise direction.

Interpretation Introduction

(b)

Interpretation: The two isomeric products formed on reaction of A with Zn(BH4)2 is to be drawn.

Concept introduction: Zincborohydride is a metal hydride reagent. It is a mild reducing agent which reduces ketones to alcohol. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The reagent used to convert the A to the single stereoisomer X is to be predicted.

Concept introduction: The chiral oxazaborolidine catalysts are enantiomeric selective reducing reagent. The carbonyl group of ketones are reduced to form one stereoisomer in the enantiomeric excess.

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Answer 3

Question

Chapter 31, Problem 31.25P

Interpretation Introduction

(a)

Interpretation: The stereogenic center at C15 is to be labeled as R or S.

Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from 1→2→3. The configuration of the compound is R and S when circle rotates in clockwise and anticlockwise direction.

Interpretation Introduction

(b)

Interpretation: The two isomeric products formed on reaction of A with Zn(BH4)2 is to be drawn.

Concept introduction: Zincborohydride is a metal hydride reagent. It is a mild reducing agent which reduces ketones to alcohol. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The reagent used to convert the A to the single stereoisomer X is to be predicted.

Concept introduction: The chiral oxazaborolidine catalysts are enantiomeric selective reducing reagent. The carbonyl group of ketones are reduced to form one stereoisomer in the enantiomeric excess.

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Answer 4

Question

Chapter 31, Problem 31.25P

Interpretation Introduction

(a)

Interpretation: The stereogenic center at C15 is to be labeled as R or S.

Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from 1→2→3. The configuration of the compound is R and S when circle rotates in clockwise and anticlockwise direction.

Interpretation Introduction

(b)

Interpretation: The two isomeric products formed on reaction of A with Zn(BH4)2 is to be drawn.

Concept introduction: Zincborohydride is a metal hydride reagent. It is a mild reducing agent which reduces ketones to alcohol. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The reagent used to convert the A to the single stereoisomer X is to be predicted.

Concept introduction: The chiral oxazaborolidine catalysts are enantiomeric selective reducing reagent. The carbonyl group of ketones are reduced to form one stereoisomer in the enantiomeric excess.

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Answer 5

Chapter 31, Problem 31.25P

Interpretation Introduction

(a)

Interpretation: The stereogenic center at C15 is to be labeled as R or S.

Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from 1→2→3. The configuration of the compound is R and S when circle rotates in clockwise and anticlockwise direction.

Interpretation Introduction

(b)

Interpretation: The two isomeric products formed on reaction of A with Zn(BH4)2 is to be drawn.

Concept introduction: Zincborohydride is a metal hydride reagent. It is a mild reducing agent which reduces ketones to alcohol. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Interpretation Introduction

(c)

Interpretation: The reagent used to convert the A to the single stereoisomer X is to be predicted.

Concept introduction: The chiral oxazaborolidine catalysts are enantiomeric selective reducing reagent. The carbonyl group of ketones are reduced to form one stereoisomer in the enantiomeric excess.

Answer 6

Chapter 31, Problem 31.25P

Interpretation Introduction

(a)

Interpretation: The stereogenic center at C15 is to be labeled as R or S.

Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from 1→2→3. The configuration of the compound is R and S when circle rotates in clockwise and anticlockwise direction.

Answer 7

Chapter 31, Problem 31.25P

Interpretation Introduction

(a)

Interpretation: The stereogenic center at C15 is to be labeled as R or S.

Concept introduction: The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom with higher atomic number is given higher priority. Complete the circle in decreasing order of priority from 1→2→3. The configuration of the compound is R and S when circle rotates in clockwise and anticlockwise direction.

Answer 8

Interpretation Introduction

(b)

Interpretation: The two isomeric products formed on reaction of A with Zn(BH4)2 is to be drawn.

Concept introduction: Zincborohydride is a metal hydride reagent. It is a mild reducing agent which reduces ketones to alcohol. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer 9

Interpretation Introduction

(b)

Interpretation: The two isomeric products formed on reaction of A with Zn(BH4)2 is to be drawn.

Concept introduction: Zincborohydride is a metal hydride reagent. It is a mild reducing agent which reduces ketones to alcohol. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer 10

Interpretation Introduction

(c)

Interpretation: The reagent used to convert the A to the single stereoisomer X is to be predicted.

Concept introduction: The chiral oxazaborolidine catalysts are enantiomeric selective reducing reagent. The carbonyl group of ketones are reduced to form one stereoisomer in the enantiomeric excess.

Answer 11

Interpretation Introduction

(c)

Interpretation: The reagent used to convert the A to the single stereoisomer X is to be predicted.

Concept introduction: The chiral oxazaborolidine catalysts are enantiomeric selective reducing reagent. The carbonyl group of ketones are reduced to form one stereoisomer in the enantiomeric excess.

Answer 12

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Answer 13

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Answer 14

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Answer 15

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Solution Summary: The author explains that the stereogenic center at C15 is labeled as R or S.

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