Nucleophilic Acyl Substitution Reaction Mechanism - Carboxylic Acid Derivatives, Organic Chemistry | Summary and Q&A

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January 12, 2017
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Nucleophilic Acyl Substitution Reaction Mechanism - Carboxylic Acid Derivatives, Organic Chemistry

TL;DR

This video explains the mechanism of nucleophilic acyl substitution reactions and how to predict the products formed when reacting different nucleophiles with acid chloride, alcohol, and amide substrates.

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Key Insights

  • 💁 Nucleophilic acyl substitution reactions involve the attack of nucleophiles on the carbonyl carbon of acid chloride, leading to the formation of carboxylic acid or carboxylate ion products.
  • 👥 The leaving group in these reactions is usually chloride, which is replaced by the desired nucleophile.
  • 💁 Acid chloride reacts with alcohol to produce esters, while reacting with ammonia or primary amines forms amides.
  • 💁 Under basic conditions, esters react with water to form carboxylate ions, while under acidic conditions, they are converted into carboxylic acids with alcohol as a side product.
  • 🥵 The addition of heat can facilitate these reactions and increase their rate.
  • 💁 Acid anhydrides can be formed by combining acid chloride with a carboxylic acid molecule.

Transcript

in this video i'm going to focus on nucleophilic acyl substitution reactions so let's say if we have an acid chloride which is a type of carboxylic acid derivative and let's react it with a negatively charged nucleophile let's use hydroxide dissolved in water now how will hydroxide react with this acid chloride what do you think is going to happen ... Read More

Questions & Answers

Q: How does the nucleophile hydroxide react with acid chloride?

Hydroxide, being negatively charged, attacks the partially positive carbonyl carbon of the acid chloride, forming a tetrahedral intermediate that later results in the formation of a carboxylic acid or carboxylate ion.

Q: What happens when acid chloride reacts with an alcohol?

Acid chloride reacts with alcohol to produce an ester and hydrogen chloride (HCl) as a side product. The chlorine atom of the acid chloride is replaced by the alkyl group of the alcohol.

Q: Can you explain the mechanism of the reaction between an amide and ammonia?

In the reaction between an amide and ammonia, the nucleophilic attack of ammonia on the carbonyl carbon forms a tetrahedral intermediate. Subsequently, the amide is deprotonated by another ammonia molecule, resulting in the formation of an amide product.

Q: How can acid chloride be converted into an anhydride?

By combining acid chloride with a carboxylic acid molecule, the chlorine atom is replaced by the carboxylic acid group, resulting in the formation of an anhydride.

Summary & Key Takeaways

  • Nucleophilic acyl substitution reactions involve reacting acid chloride with negatively charged nucleophiles, such as hydroxide or water, to produce carboxylic acid or ester products.

  • The mechanism involves the nucleophile attacking the carbonyl carbon, forming a tetrahedral intermediate that later collapses to yield the final product.

  • Acid chloride reacts with alcohol to produce esters, while reacting with ammonia or a primary amine forms amides.

  • Under basic conditions, esters react with water to yield carboxylate ions, while under acidic conditions, they are converted into carboxylic acids and alcohols are formed as side products.

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