Reactions of Aldehydes and Ketones | Summary and Q&A

TL;DR

Aldehydes and ketones undergo nucleophilic addition reactions, resulting in the formation of a product with a nucleophile attached to the carbonyl group.

Key Insights

• ❓ Aldehydes and ketones undergo nucleophilic addition reactions.
• 🫀 The carbon atom of the carbonyl group is partially positive, while the oxygen atom is partially negative.
• 👊 Nucleophiles attack the carbonyl carbon, causing a structural change from trigonal planar to tetrahedral.
• 🫀 In the presence of a proton-containing solvent, the nucleophile can acquire a hydrogen atom.
• 👥 The resulting product of nucleophilic addition has a nucleophile attached to the carbonyl group.
• ❓ Nucleophilic addition is a general reaction that occurs between aldehydes/ketones and nucleophiles.
• 🥺 Sp2 hybridization leads to the trigonal planar structure of aldehydes/ketones, while sp3 hybridization results in the tetrahedral structure of the alkoxide intermediate.

Transcript

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Questions & Answers

Q: What is the key difference in structure between aldehydes/ketones and the intermediate alkoxide formed during nucleophilic addition?

Aldehydes and ketones have a trigonal planar structure due to sp2 hybridization, while the alkoxide intermediate has a tetrahedral structure due to sp3 hybridization.

Q: What role does the nucleophile play in nucleophilic addition?

The nucleophile attacks the partially positive carbon atom of the carbonyl group, leading to the shift of the electron pair towards the oxygen.

Q: What happens to the nucleophile if the reaction occurs in a solvent containing protons?

In the presence of a proton-containing solvent, the nucleophile can acquire a hydrogen atom, resulting in the formation of a product with an -OH group.

Q: Can you explain why the carbon atom of the carbonyl group is partially positive and the oxygen atom is partially negative?

The oxygen atom is more electronegative than the carbon atom, causing it to attract electron density towards itself and acquire a partial negative charge. Conversely, the carbon atom loses electron density and becomes partially positive.

Summary & Key Takeaways

• Aldehydes and ketones contain a carbonyl group, with the oxygen atom being partially negative and the carbon atom being partially positive.

• Nucleophilic addition occurs when a nucleophile attacks the partially positive carbon atom of the carbonyl group, causing the electron pair to shift towards the oxygen.

• This results in a change in the structure from trigonal planar to tetrahedral, with the nucleophile attached to the carbon atom.

• In the presence of a proton-containing solvent, the nucleophile can acquire a hydrogen atom, leading to the formation of a product with an -OH group.