Depto. Química Orgánica

PHYSICAL AND BOND PROPERTIES OF ACID (ACYL) HALIDES

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15/07/2017
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Even though the acyl halide function bears a certain polarity, its presence in a molecule does not make much difference concerning its boiling point as compared to the corresponding alkane, i.e. it doesn't make the intermolecular forces stronger.
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Carboxylic acid derivatives can be described by three resonance forms, their relative contribution depending on the nature of L group.
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The C=O and C-L bond lengths can be understood by a higher or lower contribution of the first and third resonance forms.
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Let's take methyl chloride and acetaldehyde as the reference measurement of true single C-O and double C=O bond lengths.
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What conclusion can you draw? There should be a negligible contribution of the third resonance form.

The contribution of this third resonance form in acyl halides is the lowest in the carboxylic acid derivatives.