Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 22, Problem 14PP
Interpretation Introduction

Interpretation:

The Kiliani–Fischer reaction for the synthesis of epimeric aldoses is to be outlined and Fischer projection of D()Arabinose and D()Ribose is to be represented on the basis of given information.

Concept introduction:

舧 A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen-oxygen atom ratio of 2:1

HNO3 is an oxidizing agent.

舧 Carbohydrates are oxidized by HNO3 to give aldaric acid as a product.

舧 Aldaric acids are carbohydrates having two carboxylic acids. They are formed due to oxidation reaction of aldoses with dilute HNO3 and their general reaction can be represented as:

Organic Chemistry, Chapter 22, Problem 14PP

舧 The molecules that are nonsuperimposable or not identical with their mirror images are known as chiral molecules.

舧 A pair of two mirror images that are nonidentical is known as enantiomers, which are optically active.

舧 The stereoisomers that are nonsuperimposable on each other and not mirror images of each other are known as diastereomers.

舧 The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.

舧 Compounds that have a plane of symmetry tend to exist in meso forms. A meso form arises when the two stereoisomers produce superimposable images, and hence, compounds having meso forms are optically inactive.

舧 The Kiliani-Fischer reaction is used for increasing the number of carbon atoms of the respective aldoses, thereby, lengthening the carbon chain of the compound. It is an effective and economic process for synthesizing monosaccharides through the hydrolysis of a cyanohydrin. Thus, it lengthens the carbon chain of the aldose by one carbon atom. It is used to produce epimers of higher aldoses from a lower aldose, that is, a single aldose produces a mixture of two diastereomeric sugars called epimers.

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Experiment 1 Data Table 1: Conservation of Mass - Initial Mass Data Table 1 Data Table 2 Data Table 3 Data Table 4 Panel 1 Photo 1 Data Table 5 Reaction Mass of test tube and 5.0% HC₂H₂O2 (g) # (A) (B) Mass of NaHCO, (g) Mass of balloon and NaHCO, (g) (C) 0.10 1 0829 14.38g 0.20 2 0.929 14.29g 0.35 1.00g 3 14.25g 0.50 1.14g 14.29 Experiment 1 Data Table 2: Moles of HC2H3O2 Reaction Volume of Mass of Moles of HC₂H₂O₂ 5.0% Vinegar (g) (ML) 5.0 0.25 0042 mol 2 5.0 0.25 0042 mol 3 5.0 0.25 0042 mol 5.0 0.25 0042 mol Experiment 1 Data Table 3: Moles of NaHCO3 Reaction Mass of NaHCO (g) 10g 20g 35g 50g Experiment 1 Data Table 4: Theoretical Yield of CO₂ Reaction # 1 2 3 Experiment 1 Total mass before reaction (g) (D=A+C) 15.29 15.21g 15.25g 15.349 Exercise 1 Data Table 1 Data Table 2 Data Table 3 Data Table 4 Panel 1 Photo 1 Data Table 5 Exercise 1- Data Table 1 Data Table 2 DataTable 3 Data Table 4 Panel 1 Photo 1 Data Table 5 Exercise 1- Moles of NaHCO 0012 mol 0025 mol 0044 mol 0062 mol…
The chemical reaction you investigated is a two-step reaction. What type of reaction occurs in each step? How did you determine your answer?
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