Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Chapter 13, Problem 13.28P
Interpretation Introduction

Interpretation:

Using the given parameters from a partial molecule, the correct NMR spectrum has to be sketched.

Concept Introduction:

The 1H NMR spectrum of a compound provides some vital information that is required to predict the structure of the compound.  The chemical shift values can predict the groups that are present in the molecule.  The splitting of signals by the (N+1) rule predicts the number of hydrogens or protons attached to the adjacent carbon in a carbon chain of a compound.  With this information, the structure of the compound can be predicted.

The single 1H NMR signal is split into multiple peaks called the multiplicity of the signal.  Splitting of signals is done according to the (N+1)) rule.  N is the number of adjacent nonequivalent protons.  According to the (N+1) rule, for a proton-coupled with N adjacent nonequivalent protons, the signal split into (N+1) peak.  The splitting is mutual.  Splitting occurs only due to nonequivalent protons that are the protons present in the different chemical environment.

The distance between any two adjacent peaks is called coupling constant in hertz represented as J.  The value of coupling constant for two protons coupling with each other is same.  Thus the coupling constant gives vital information about the adjacent groups or protons because protons on adjacent carbons have a similar coupling constant.

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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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