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Organic Chemistry: Acid Halides

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Winnie Yu

on 12 October 2012

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Transcript of Organic Chemistry: Acid Halides

Winnie Yu & Clement Zhang Acid Halides Winnie Yu &
Clement Zhang
Period 3 &4 What are acid
halides, as acid derivatives of carboxylic acids? 1. Identify the longest carbon chain and name it with the proper prefix and suffix, respectively.
2. Identify the location of any acyl group (RCO-) bonded to a halogen atom.
3. Drop the suffix -oic acid for the parent carboxylic acid, and replace it with -oyl halide. For hydrocarbons, drop the -e ending and replace it with -oyl halide.
4. Following this step, add the halogen names as a separate word. (Bromide, chloride, fluoride, iodide) Naming Acid Halides Cannot dissolve in water because they react violently with it, but can be reacted with water to form carboxylic acid
Hydrolyze in moist air and have sharp odors, which causes it to be irritating to mucous membranes, eyes, and skin Properties as intermediates during the synthesis of other organic compounds since their halogen atoms can be easily replaced by other groups
used primarily in organic synthesis reactions to introduce acyl group into compounds
many kinds of carbonyl compounds contain acyl group - aldehydes, ketones, carboxylic acids, esters, amides... Uses http://chemistry.boisestate.edu/people/richardbanks/organic/nomenclature/acidhalidenomenclature1.htm
Fundamentals of Organic Chemistry (Fifth Edition) by John McMurry (pg 277, 307) Bibliography Acid halides, also known as "acyl halides," are carboxylic acid derivatives in which the -OH functional group is replaced with a halogen atom. This functional group is easily recognized for formula R-COX. R - represents alkyl group
CO - represents carbonyl group
X - represents halide Simple? Examples: (We will focus more on acyl chlorides throughout this lesson, one of the most commonly known forms of acid halides) longest chain: 2 = ethane
halide: chloride ethanoyl chloride longest chain: 4 = butane
halide: chloride butanoyl chloride More examples! Try these trick(ier) ones! Do Now: What are organic acids also known as? Provide the general formula for this functional group and the IUPAC rules for naming it.

Now...what do you think the term acid derivatives means? Keep in mind: Follow regular nomenclature rules when there are additional functional groups or double and triple bonds in the structure by giving them priority and placing them in alphabetical order correctly. Example: Acyl Chlorides Acyl chlorides, such as ethanoyl chloride, are polar molecules, therefore they have dipole-dipole forces, as well as london dispersion forces.
However, it does not have any hydrogen bonds. This makes its boiling point and melting point lower than similar carboxylic acids. (Acetic acid would boil at 118 °C, but acetyl chloride would at 51 °C.)
Ethanoyl chloride is a colorless fuming liquid. Its strong smell includes a mixture of vinegar (ethanoic acid) and hydrogen chloride gas becauce of a reaction with the water vapor in the air. Ethanoyl Chlorides Review! Organic acids are also known as carboxylic acids.
General formula: R-COOH.
Suffix: -oic acid / -carboxylic acid Acid derivatives have compounds where the -OH group in the acid is replaced by something else. Acyl chlorides are one example of an acid derivative. In this case, the -OH group is replaced by a chlorine atom. water, to form carboxylic acid (industrial synthesis of acetic acid) alcohol, to form ester amine, to form amide Acyl halides react with.... note: HX is a hydrogen halide.
e.g. if the acyl halide was acyl chloride, hydrogen chloride would be formed in the reaction. However... acid halides are most widely known for the production of acetic acid! (as mentioned before)

benzoyl bromide cyclohexanecarbonyl
chloride 3,3,3-trifluoropropanoyl
chloride (from cyclohexanecarboxylic acid)
note: for cyclic compounds, the suffix should be replaced with - carbonyl halide (acetyl chloride - from acetic acid)
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