The structure of D-erythrose has to be identified from the given structures. Concept introduction: The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules. According to Cahn-Ingold-Prelog system, The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on. For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

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Answer 1

Question

Chapter 4.15, Problem 62P

(a)

Interpretation Introduction

Interpretation:

The structure of D-erythrose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

(b)

Interpretation Introduction

Interpretation:

The structure of D-threose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

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The following compound has two asymmetric centers and four stereoisomers. Two of these are d-erythrose and d-threose, which are naturally occurring sugars. The configuration of d-erythrose is (2R,3R), and the configuration of d-threose is (2S,3R). a. Which structure represents d-erythrose? b. Which represents d-threose?

Consider alanine a. How many chiral centers? b. How many stereoisomers? c. Draw the fischer projection for each stereoisomer and determine the absolute configuration for each chiral center.

1. Identify the anomeric carbons on sucrose and explain how they are different from lactose and cellulose. 2. On Wikipedia (image pictures below) sucrose is labeled β-D-Fructofuranosyl α-D-glucopyranoside. But the anomeric carbon has the oxygen pointing down and other stereocenters inverted from that of fructose. Did Wikipedia incorrectly name it? Or can you explain why this is the case using structures of sucrose, fructose and glucose…

Answer 2

Question

Chapter 4.15, Problem 62P

(a)

Interpretation Introduction

Interpretation:

The structure of D-erythrose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

(b)

Interpretation Introduction

Interpretation:

The structure of D-threose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

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Answer 3

Question

Chapter 4.15, Problem 62P

(a)

Interpretation Introduction

Interpretation:

The structure of D-erythrose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

(b)

Interpretation Introduction

Interpretation:

The structure of D-threose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

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Answer 4

Question

Chapter 4.15, Problem 62P

(a)

Interpretation Introduction

Interpretation:

The structure of D-erythrose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

(b)

Interpretation Introduction

Interpretation:

The structure of D-threose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

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See solution

Answer 5

Chapter 4.15, Problem 62P

(a)

Interpretation Introduction

Interpretation:

The structure of D-erythrose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

(b)

Interpretation Introduction

Interpretation:

The structure of D-threose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

Answer 6

Chapter 4.15, Problem 62P

(a)

Interpretation Introduction

Interpretation:

The structure of D-erythrose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

Answer 7

Chapter 4.15, Problem 62P

(a)

Interpretation Introduction

Interpretation:

The structure of D-erythrose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The structure of D-threose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The structure of D-threose has to be identified from the given structures.

Concept introduction:

The configuration of stereoisomer is determined by Cahn-Ingold-Prelog system rules.

According to Cahn-Ingold-Prelog system,

The group attached to asymmetric center should be ranked based on the atomic number of atom which directly connected to asymmetric center. The higher the atomic number of atom, higher the priority. If there is tie, then consider the next atoms attached to the connected atom and so on.

For Fischer projection formula: Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is bonded in horizontal line, then the configuration is assigned as just reverse.

Answer 10

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Answer 12

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Answer 13

Ch. 4.1 - Prob. 2P Ch. 4.1 - Prob. 3P Ch. 4.1 - Prob. 4P Ch. 4.1 - Prob. 5P Ch. 4.1 - Which of the roll owing compounds have a dipole...Ch. 4.2 - Draw and label the E and Z isomers for each of the...Ch. 4.2 - Assign relative priorities to each set of...Ch. 4.2 - Tamoxifen slows the growth of some breast tumors...Ch. 4.2 - Prob. 10P Ch. 4.2 - Name each of the following:

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