ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 24.10, Problem 11P
Interpretation Introduction

Interpretation:

The possible number of ketotetroses is to be determined and their Fischer projections are to be drawn.

Concept introduction:

A ketotetroses is a carbohydrate with a four-carbon chain and a ketone functional group. It is a type of monosaccharide.

The possible number of ketotetroses can be calculated on the basis of number of chiral centers.

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a. What is the eluent used in the column chromatography here (a “silica plug filtration” is essentially a very short column)? b. The spectroscopy of compound 5b is described in the second half of this excerpt, including 1H-NMR and 13C-NMR (which you will learn about in CHEM 2412L), MS (which you will learn about later in CHEM 2411L) and IR. One of the IR signals is at 3530 cm-1. What functional group does this indicate might be present in compound 5b?
Steps and explanations. Also provide, if possible, ways to adress this kind of problems in general.
a. The first three lines of this procedure describe the reaction used to make compound 5b. In the fourth line, hexane and sodium bicarbonate are added. What organic lab technique is being used here?  b. What is the purpose of the Na2SO4?  c. What equipment would you use to “concentrate [a solution] under reduced pressure”?
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