Question:

Which one of the following produces acyl halide by treatment with $ {PCl_5}$?

Updated On: Jul 29, 2023

Alcohols
Esters
Acids
Carbonyl compounds

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The Correct Option is C

Solution and Explanation

Acid chlorides would be created in the products of the reaction of PCl₅ with the specified acid. The common term for acyl halide, when chlorine is the halogen, is acid chloride.

There are other comparable compounds where the acid's -OH group is switched out for another one, leaving the acyl carbon in a +3 oxidation state. These substances are referred to as acid derivatives. One type of acid derivative is acyl halides, also referred to as acid halides. The most typical acid halide, chlorine, has been utilized in place of the -OH group in this case.

A hydrocarbon group called the acyl group is joined to a carbon-oxygen double bond.

Typically, only alkyl groups are allowed to have the "R" group. But it may be a group built around a benzene ring.

A few examples are– ethanoyl chloride (CH₃COCl), and propanoyl chloride (CH₃CH₂COCl).

An acyl halide, like ethanoyl chloride, is a fuming, colourless liquid. Ethanoyl chloride has a strong odour that is a combination of the acidic odour of vinegar (ethanoic acid) and the pungent odour of hydrogen chloride gas.

As they react with water to form hydrogen halides and carboxylic acids, acyl halides do not dissolve in water.
A common example is ethanoyl chloride, which is a polar molecule and boils at 51°C.
As a result, it has van der Waals dispersion forces as well as the dipole-dipole attraction between its molecules.
It does not, however, create hydrogen bonds.
As a result, it has a higher boiling point than an alkane of comparable size like ethane, which boils at -88.5°C, but not as high as alcohol of comparable size like ethanol, which boils at 78.37°C.
As acyl halides are so reactive, another functional group always takes the place of the halogen atom in each of their reactions.

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Notes on Haloalkanes and Haloarenes

Concepts Used:

Haloalkanes and Haloarenes

The hydrocarbons such as Haloalkanes and Haloarenes are the ones, in which one or more hydrogen atoms are replaced with halogen atoms. The main difference between Haloalkanes and Haloarenes is that Haloalkanes are derived from open chained hydrocarbons, also called alkanes, and Haloarenes are derived from aromatic hydrocarbons.

Haloalkanes have hydrocarbons made up of aliphatic alkanes and one or more hydrogen atoms replaced by halogens (elements such as Chlorine, Bromine, Fluorine, Iodine, etc.) whereas, haloarenes consist of aromatic ring or rings and one or more hydrogen atoms replaced by halogens.
In haloalkanes, the halogen atom is attached to the sp³ hybridized carbon atom of the alkyl group whereas, in haloarenes, the halogen atom is attached to the sp³ hybridized carbon atom of the alkyl group.
Haloalkanes are saturated organic compounds where all the chemical bonds are attached to the carbon atom with single bonds and a single carbon atom is attached to the Halogen atom, whereas, the haloarenes differ from Haloalkanes by their method of preparation and properties.
Haloalkanes are made by aliphatic alkanes by the process of free radical halogenation, whereas, haloarenes are made by direct halogenation of aromatic rings.
Haloalkanes are odorless compounds, whereas, haloarenes have a sweet odor.
Haloalkanes precipitate in SN² substitution reactions, whereas, haloarenes do not precipitate in SN² substitution reactions.
Example of haloalkanes is CH₃Cl (Methyl Chloride) and CH₃CH₂Br (Ethyl Bromide) and the example of haloarenes is Chlorobenzene, Bromobenzene.