Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 17, Problem 17.47AP
Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the reaction of 2-hexyne with strong base (NHCH2CH2CH2NH2) is to be predicted. The explanation for the fact that the corresponding reaction is irreversible reaction is to be stated.

Concept introduction:

The isomerization process of converting internal alkynes into terminal alkynes is known as acetylene zipper reaction. The acetylene zipper reaction required a strong base. A diamine ion is used in the reaction to transfer proton from one carbon atom to another carbon atom.

Interpretation Introduction

(b)

Interpretation:

The product of reaction of 3-methyl-4-octyne with strong base (NHCH2CH2CH2NH2) is to be predicted.

Concept introduction:

The isomerization process of converting internal alkynes into terminal alkynes is known as acetylene zipper reaction. The acetylene zipper reaction required a strong base. A diamine ion is used in the reaction to transfer proton from one carbon atom to another carbon atom.

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The saccharide shown here is present in some plant-derived foods.            (a) Indicate the anomeric carbon atom(s) in this structure by drawing a circle around the atom(s) or by drawing an arrow pointing to the atom(s).               (b) Would this saccharide give a positive result with Benedict’s reagent? Why or why not?               (c) Would this saccharide give a positive result with Barfoed’s reagent? Why or why not?             (d) Would this saccharide give a positive result with Seliwanoff’s reagent? Why or why not?               (e) In a separate set of experiments, the saccharide solution was treated with a reagent that breaks glycosidic bonds. After this treatment, would any of the three assays give different results? Be sure to indicate which assay results would be different and give a reason.
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