ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 24, Problem 26P
Interpretation Introduction

Interpretation:

The structural formulas for the given compounds are to be provided.

Concept Introduction:

In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively.

The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.

Expert Solution & Answer
Check Mark

Answer to Problem 26P

Solution:

a) The structural formula of ()-Xylose is C5H10O5 and the Fischer projection is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  1

b) The structural formula for the xylitol is C5H12O5 and Fischer projection is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  2

c) The structural formula of β-D-Xylopyranose is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  3

d) The structural formula of α-L-Xylofuranose is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  4

e) The structure of Methylα-L-xylofuranoside is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  5

f) The Fischer projection formula for the given compound is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  6

g) The structure of the given compound is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  7

h) The structure of the given compound is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  8

i) The Fischer projection formula for the given compound is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  9

Explanation of Solution

a) The given structure of (+)-D-xylose is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  10

In, (+)-D-xylose, hydroxyl group present on the fourth carbon is in right side.

L and D indicate the absolute configuration of a compound. If hydroxy group attached with chiral centre is to the right side and present on the bottom, then the carbohydrate is in D form but if hydroxy group is present to the left side then the carbohydrate is in L-form.

The name of the given compound is ()-Xylose. The Fischer projection of ()-Xylose is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  11

b) The given compound is xylitol.

The alcohol derivative of xylose is xylitol in which the reduction of aldehyde group to alcohol takes place. Thus, the Fischer projection formula for the xylitol is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  12

c) The given compound is β-D-Xylopyranose.

Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose.

The given compound is formed when C1 and C5 carbon unit of D-Xylose reacts with each other. The formation of β-D-Xylopyranose from D-Xylose is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  13

Thus, the structural formula of β-D-Xylopyranose is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  14

d) The given compound is α-L-Xylofuranose.

L and D indicate the absolute configuration of a compound. If hydroxy group attached with chiral centre is to the right side and present on the bottom, then the carbohydrate is in D form but if hydroxy group is present to the left side then the carbohydrate is in L-form.

The given compound is formed when C1 and C4 carbon unit of L-Xylose reacts with each other. The formation of α-L-Xylofuranose from L-Xylose is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  15

Thus, the structural formula of α-L-Xylofuranose is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  16

e) The given compound is Methylα-L-xylofuranoside.

The given compound is formed when hydroxyl group is replaced by methoxy group as shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  17

Thus, the structure of Methylα-L-xylofuranoside is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  18

f) The given compound is D-Xylonicacid.

The oxidation of D-xylose into acid results in the formation of D-Xylonicacid. Thus, the Fischer projection formula for the given compound is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  19

g) The given compound is δ-Lactone.

Lactones are class of organic compound which contain -OCO- as part of the ring. The formation of δ-Lactone takes place from D-Xylonicacid. When hydroxyl group that is present on C1 and C5 carbon unit of D-Xylonicacid combine together results in the formation of δ-Lactone as shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  20

Thus, the structure of the given compound is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  21

h) The given compound is γ-Lactone.

Lactones are class of organic compound which contain -OCO- as part of the ring. The formation of γ-Lactone takes place from D-Xylonicacid. When hydroxyl group that is present on C1 and C4 carbon unit of D-Xylonicacid combine together results in the formation of γ-Lactone as shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  22

Thus, the structure of the given compound is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  23

i) The given compound is Xylaric acid.

The oxidation of D-xylose into acid results in the formation of Xylaric acid. To form Xylaric acid, the oxidation of aldehyde group and hydroxyl group of D-xylose into acid take place Thus, the Fischer projection formula for the given compound is shown below.

ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE, Chapter 24, Problem 26P , additional homework tip  24

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