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Rank the following carbonyl compounds in order of increasing reactivity towards nucleophiles: NH2 I Br II III IV

Rank the following carbonyl compounds in order of increasing reactivity towards nucleophiles: NH2 I Br II III IV

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**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.
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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