(a) Interpretation: Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated. Concept introduction: Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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3. SYNTHESIS. Propose a sequence of synthetic steps (FGI) that convert the starting material (SM) into the Target molecule. For each FGI in your proposed synthesis, specify the reagents / conditions, and draw the product(s) of that FGI. DO NOT INCLUDE the FGI mxn in the answer you submit. If an FGI requires two reagent sets, specify the order in which the reagent sets are added, e.g., i) Hg(OAc)2 / H₂O; ii) NaBH4/MeOH. Indicate the stereochemistry (if any) of the products of each FGI. FGI 1. Me Starting Material Source of all carbons in the Target molecule (can use multiple copies) Me Me Target molecule + enantiomer

curved arrows are used to illustate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction mechanism steps

Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

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Answer 5

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 6

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 7

Chapter 24, Problem 24.4P

Interpretation Introduction

(a)

Interpretation:

Whether the configuration of the aldose, 6-deoxyglucose is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Whether the configuration of glucose enantiomer with R configuration at carbon -3 is D or L is to be stated.

Concept introduction:

Aldoses are the carbohydrates in which an aldehyde group is present. The aldehyde carbon is numbered one in Fischer projection. A carbohydrate consists of six carbon atoms chain and an aldehyde group is known as aldohexose. Stereoisomers are the isomers which have same molecular formula but differ in the orientation of atoms or molecules in space. A stereoisomer which rotates the plane of polarized light towards right is a dextrorotatory compound and is represented by D or + signs. A stereoisomer which rotates the plane of polarized light towards left is a levorotatory compound and is represented by L or − signs.

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Prob. 24.3P Ch. 24 - Prob. 24.4P Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Prob. 24.7P Ch. 24 - Prob. 24.8P Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

Solution Summary: The author explains the structure of the aldose, 6-deoxyglucose, and the stereoisomers of glyceraldehydes.

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Chapter 24 Solutions