ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 21, Problem 58DSP
Interpretation Introduction

Interpretation:

The major organic product(s) of the given reaction is to be predicted.

Concept Introduction:

Carboxylic acids in presence of the reagent NaH, THF followed by LDA yields the acid dianions in which the negative charge resides on both the oxygen atoms in the original carboxylic acid.

However, the dianion formed has carbanionic character and it can potentially act as a nucleophile to create a new carbon-carbon single bond.

The dianions formed when treated with primary or methyl halides the alkylation of acid dianions takes place.

The new carbon-carbon single bond in these reactions is formed between the carbon atom bearing the halogen atom in the given alkyl halide and the alpha carbon atom in the given carboxylic acid.

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Transmitance 3. Which one of the following compounds corresponds to this IR spectrum? Point out the absorption band(s) that helped you decide. OH H3C OH H₂C CH3 H3C CH3 H3C INFRARED SPECTRUM 0.8- 0.6 0.4- 0.2 3000 2000 1000 Wavenumber (cm-1) 4. Consider this compound: H3C On the structure above, label the different types of H's as A, B, C, etc. In table form, list the labeled signals, and for each one state the number of hydrogens, their shifts, and the splitting you would observe for these hydrogens in the ¹H NMR spectrum. Label # of hydrogens splitting Shift (2)
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ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE

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