Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Reactions at the Alpha Carbon Atom
The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an …
Question
**Title: Reactivity of Carbonyl Compounds Towards Nucleophiles** **Objective:** Understand the relative reactivity of different carbonyl compounds when interacting with nucleophiles. **Compounds Presented:** 1. **Compound I:** - Structure: Contains a carbonyl group (C=O) attached to a methyl group (CH₃) and an amine (NH₂). - Commonly an amide. 2. **Compound II:** - Structure: Simple aldehyde with a carbonyl group (C=O) attached to a hydrogen (H) and a methyl group (CH₃). - Known as an aldehyde. 3. **Compound III:** - Structure: Carbonyl group (C=O) bonded to a bromine atom (Br) and a methyl group (CH₃). - This is an acyl bromide. 4. **Compound IV:** - Structure: Features two carbonyl groups (C=O) attached to an oxygen atom, forming an ester linkage. - Known as an acid anhydride. **Task:** Rank the compounds in order of increasing reactivity towards nucleophilic attack. **Guide:** - **Amides (I):** Least reactive due to resonance stabilization and poor leaving group (NH₂⁻). - **Esters (IV):** Moderately reactive; less stabilized than amides, but the OR group is a better leaving group than NH₂⁻. - **Aldehydes (II):** More reactive as they are less sterically hindered compared to ketones. - **Acyl Bromides (III):** Highly reactive due to the excellent leaving ability of the bromide ion. **Conclusion:** Rank in order of increasing reactivity: I < IV < II < III This information helps in predicting reaction pathways and mechanisms in organic synthesis involving carbonyl compounds.
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Transcribed Image Text:**Title: Reactivity of Carbonyl Compounds Towards Nucleophiles** **Objective:** Understand the relative reactivity of different carbonyl compounds when interacting with nucleophiles. **Compounds Presented:** 1. **Compound I:** - Structure: Contains a carbonyl group (C=O) attached to a methyl group (CH₃) and an amine (NH₂). - Commonly an amide. 2. **Compound II:** - Structure: Simple aldehyde with a carbonyl group (C=O) attached to a hydrogen (H) and a methyl group (CH₃). - Known as an aldehyde. 3. **Compound III:** - Structure: Carbonyl group (C=O) bonded to a bromine atom (Br) and a methyl group (CH₃). - This is an acyl bromide. 4. **Compound IV:** - Structure: Features two carbonyl groups (C=O) attached to an oxygen atom, forming an ester linkage. - Known as an acid anhydride. **Task:** Rank the compounds in order of increasing reactivity towards nucleophilic attack. **Guide:** - **Amides (I):** Least reactive due to resonance stabilization and poor leaving group (NH₂⁻). - **Esters (IV):** Moderately reactive; less stabilized than amides, but the OR group is a better leaving group than NH₂⁻. - **Aldehydes (II):** More reactive as they are less sterically hindered compared to ketones. - **Acyl Bromides (III):** Highly reactive due to the excellent leaving ability of the bromide ion. **Conclusion:** Rank in order of increasing reactivity: I < IV < II < III This information helps in predicting reaction pathways and mechanisms in organic synthesis involving carbonyl compounds.
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