Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16.8, Problem 12P
Interpretation Introduction

Interpretation:

The products (in chair conformers formed), from the reaction of β- D-galactose with ethanol and HCl have to be drawn.

Concept Introduction:

Glycoside formation: carbohydrates react with an alcohol in acid which produce both anomers acetals are formed, if alkoxy group points down then it is α, alkoxy group points up then it is β.

Sugar molecule in which hydroxyl groups of first and sixth carbon atom are on the same side is known as α sugar, otherwise, β sugar. Hydroxyl group of α-sugar present on right side in Fischer projection is represented down in Haworth projection and at axial position in chair conformation.

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Part II. xiao isolated a compound TAD (Ca H 10 N₂) from tobacco and obtained its IR spectrum. Xiao proposed a chemical structure shown below: % Transmittance 4000 3500 3000 2500 2000 Wavenumber (cm-1) 1500 1000 (a) Explain why her proposed structure is inconsistent with the IR spectrum obtained (b) TAD exists as a tautomer of the structure xiao proposed. Draw the structure and explain why it is more compatible with the obtained spectrum. (C) what is the possible source for the fairly intense signal at 1621cm1
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