Butanal is an aldehyde compound with the chemical formula CH3CH2CH2CHO. It is a colorless, flammable liquid with a pungent, fruity odor. Butanal is an important organic compound that is relevant in the context of naming aldehydes and ketones, spectroscopy of aldehydes and ketones, and carbonyl condensations, specifically the aldol reaction.
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Butanal is the common name for the aldehyde with four carbon atoms and the formula CH3CH2CH2CHO.
In the IUPAC naming system, butanal is named as the aldehyde of butane, with the carbonyl group (C=O) located at the first carbon atom.
Butanal exhibits characteristic aldehyde properties, such as the ability to undergo nucleophilic addition reactions and oxidation to carboxylic acids.
The carbonyl carbon in butanal is sp2 hybridized, leading to a planar structure and a bond angle of approximately 120 degrees.
Butanal can participate in the aldol reaction, a type of carbonyl condensation, to form larger aldol products.
Review Questions
Explain how the IUPAC naming system is used to name butanal.
In the IUPAC naming system, butanal is named as the aldehyde of butane, with the carbonyl group (C=O) located at the first carbon atom. The name is derived by taking the root name of the parent alkane (butane) and adding the suffix '-al' to indicate the presence of the aldehyde functional group. This systematic approach to naming aldehydes ensures a clear and unambiguous identification of the compound's structure.
Describe the key spectroscopic features that would be observed for butanal in the context of 19.14 Spectroscopy of Aldehydes and Ketones.
In the context of 19.14 Spectroscopy of Aldehydes and Ketones, butanal would exhibit characteristic spectroscopic signals. In the $^1$H NMR spectrum, butanal would show signals for the four methylene (CH$_2$) groups and the aldehyde proton (CHO). The carbonyl carbon would appear as a distinct signal in the $^{13}$C NMR spectrum, typically around 200 ppm. Additionally, the IR spectrum of butanal would display a characteristic absorption band around 1720 cm$^{-1}$ corresponding to the C=O stretching vibration of the aldehyde group.
Explain how butanal can participate in the aldol reaction, as described in 23.1 Carbonyl Condensations: The Aldol Reaction.
In the context of 23.1 Carbonyl Condensations: The Aldol Reaction, butanal can undergo the aldol reaction, a type of carbonyl condensation. As an aldehyde, butanal possesses a hydrogen atom attached to the carbonyl carbon, which can be removed by a base to generate an enolate intermediate. This enolate can then react with another carbonyl compound, such as another aldehyde or a ketone, to form a new, larger aldol product. The aldol reaction allows for the synthesis of more complex molecules from simpler carbonyl compounds like butanal, making it a versatile tool in organic synthesis.