Nomenclature of Carboxylic Acid Derivatives

Summary

This video script offers an in-depth tutorial on the nomenclature of carboxylic acid derivatives, including acid chlorides, esters, and amides. It reviews the basic naming conventions for carboxylic acids and then delves into the specifics of naming these derivatives, emphasizing the importance of the carbonyl carbon, substituent placement, and the use of IUPAC and common nomenclature systems. The script also covers the naming of anhydrides, highlighting both symmetrical and unsymmetrical cases, providing a comprehensive guide for understanding and applying the naming rules in organic chemistry.

Takeaways

• 😀 The video discusses the basic nomenclature of carboxylic acid derivatives, building on the nomenclature of carboxylic acids.
• 🔍 Carboxylic acids are named based on the number of carbons, with specific IUPAC names for 1-6 carbons and common names like formic, acetic, propionic, butyric, valeric, and caproic acids.
• 📚 The mnemonic 'FACT to all people better value chemistry' helps remember the common names of the first six carboxylic acids.
• 🌐 For acid chlorides, the IUPAC name involves dropping 'acid' and adding 'yl chloride', while the common name involves using 'alpha', 'beta', 'gamma' for the positions of substituents.
• 🔄 When dealing with cyclic compounds, the ring is the parent, and the carbon of the acid chloride is not counted as part of the parent, leading to a different naming approach.
• 🍋 Esters are named by specifying the R group on the oxygen, followed by the parent chain name with 'oic acid' replaced by 'oate'.
• 🔗 In the case of esters, the IUPAC name involves the R group and the parent chain, while the common name involves the parent carboxylic acid with 'ic' replaced by 'ate'.
• 💧 Amides are named by changing the 'oic acid' ending to 'amide', and any substituents on nitrogen are alphabetized with other substituents.
• 🔬 For amides, the common name involves dropping 'ic acid' and replacing it with 'amide', and any substituents are listed before the parent name.
• 🔗 Anhydrides are formed by the dehydration of two carboxylic acids and are named by combining the names of the two acids, replacing the 'ic acid' ending with 'anhydride'.
• 🔄 Unsymmetrical anhydrides require identifying the two corresponding carboxylic acids and naming them in alphabetical order with 'anhydride' at the end.

Q & A

What is the basic topic of the video?

The video discusses the nomenclature of carboxylic acid derivatives, including acid chlorides, esters, amides, and anhydrides.

What is the IUPAC name for a four-carbon carboxylic acid?

The IUPAC name for a four-carbon carboxylic acid is butanoic acid.

What is the common name for a four-carbon carboxylic acid?

The common name for a four-carbon carboxylic acid is butyric acid.

How do you name an acid chloride derivative?

To name an acid chloride derivative, you drop the 'ic' from the carboxylic acid name and add 'yl chloride' or 'yl bromide/iodide' depending on the halogen present.

What is the IUPAC name for an ester with a methyl group and a five-carbon chain?

The IUPAC name for such an ester is methyl pentanoate.

What is the common name for an ester derived from butyric acid and an ethyl group?

The common name for this ester is ethyl butyrate.

How is the nomenclature of an ester on a ring different from a regular ester?

For an ester on a ring, the ring is named first as a cycloalkane, and then the ester group is designated with the R group, followed by the term 'carboxylate'.

What is the IUPAC name for an amide with a five-carbon chain?

The IUPAC name for an amide with a five-carbon chain is pentanamide.

How do you name an anhydride formed from two molecules of acetic acid?

The anhydride formed from two molecules of acetic acid is named acetic anhydride or ethanoic anhydride in IUPAC nomenclature.

What is the difference between naming symmetrical and unsymmetrical anhydrides?

For symmetrical anhydrides, the name of the single carboxylic acid is used with the suffix 'anhydride'. For unsymmetrical anhydrides, the names of the two different carboxylic acids are combined in alphabetical order, followed by 'anhydride'.

How do you name an amide with N-methyl and N-propyl groups on the nitrogen?

The amide is named by alphabetizing the alkyl groups on nitrogen and then combining them with the parent carboxylic acid name, changing the 'ic' or 'oic' ending to 'amide'.

What is the common abbreviation for N,N-dimethylformamide?

The common abbreviation for N,N-dimethylformamide is DMF.