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Explain how you could distinguish between the following two compounds using qualitative tests and NMR. Your explanation should include which test(s) you would use and the expected results and key differences that would be present in the H-NMR OH HO. В

Explain how you could distinguish between the following two compounds using qualitative tests and NMR. Your explanation should include which test(s) you would use and the expected results and key differences that would be present in the H-NMR OH HO. В

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: Distinguishing Between Two Organic Compounds Using Qualitative Tests and NMR** **Overview** In this educational material, we will explore how to distinguish between two given organic compounds using qualitative tests and Nuclear Magnetic Resonance (NMR) spectroscopy. The compounds in question are presented as structures in the diagram below: **Diagram:** 1. **Compound A**: A benzene ring substituted with a ketone group (C=O) at the meta position relative to a hydroxyl group (OH). 2. **Compound B**: A benzene ring substituted with an aldehyde group (CHO) at the meta position relative to a hydroxyl group (OH). **General Approach** - **Qualitative Tests:** - **Compound A** (Ketone): - Ketones generally do not react with Tollens' reagent, which is used to test for aldehydes. - Will show different reactions in Brady’s test (2,4-DNPH) compared to aldehydes. - **Compound B** (Aldehyde): - Aldehydes react with Tollens' reagent to produce a silver mirror. - Also reacts with Fehling’s solution and Benedict's solution, turning them from blue to red. - **NMR Spectroscopy:** - **Compound A**: - Expected to show a deshielded peak for the hydrogen atoms on the benzene ring due to the electron-withdrawing effects of the ketone and hydroxyl groups. - **Compound B**: - Expected to show a distinct peak for the aldehyde proton (usually around 9-10 ppm). - Aromatic hydrogen peaks will be influenced by the electron-withdrawing nature of both the aldehyde and hydroxyl groups. **Detailed Explanation of Qualitative Tests:** 1. **Tollens' Reagent:** - Differentiates between aldehydes and ketones. - **Positive Test**: Formation of a silver mirror indicating the presence of an aldehyde (Compound B). - **Negative Test**: No reaction, indicating a ketone (Compound A). 2. **Brady’s Test (2,4-Dinitrophenylhydrazine):** - Both aldehydes and ketones form a yellow/orange/red precipitate. - While it does not distinguish between the two alone, the reaction can be followed by another test for confirmation.
Transcribed Image Text:**Title: Distinguishing Between Two Organic Compounds Using Qualitative Tests and NMR** **Overview** In this educational material, we will explore how to distinguish between two given organic compounds using qualitative tests and Nuclear Magnetic Resonance (NMR) spectroscopy. The compounds in question are presented as structures in the diagram below: **Diagram:** 1. **Compound A**: A benzene ring substituted with a ketone group (C=O) at the meta position relative to a hydroxyl group (OH). 2. **Compound B**: A benzene ring substituted with an aldehyde group (CHO) at the meta position relative to a hydroxyl group (OH). **General Approach** - **Qualitative Tests:** - **Compound A** (Ketone): - Ketones generally do not react with Tollens' reagent, which is used to test for aldehydes. - Will show different reactions in Brady’s test (2,4-DNPH) compared to aldehydes. - **Compound B** (Aldehyde): - Aldehydes react with Tollens' reagent to produce a silver mirror. - Also reacts with Fehling’s solution and Benedict's solution, turning them from blue to red. - **NMR Spectroscopy:** - **Compound A**: - Expected to show a deshielded peak for the hydrogen atoms on the benzene ring due to the electron-withdrawing effects of the ketone and hydroxyl groups. - **Compound B**: - Expected to show a distinct peak for the aldehyde proton (usually around 9-10 ppm). - Aromatic hydrogen peaks will be influenced by the electron-withdrawing nature of both the aldehyde and hydroxyl groups. **Detailed Explanation of Qualitative Tests:** 1. **Tollens' Reagent:** - Differentiates between aldehydes and ketones. - **Positive Test**: Formation of a silver mirror indicating the presence of an aldehyde (Compound B). - **Negative Test**: No reaction, indicating a ketone (Compound A). 2. **Brady’s Test (2,4-Dinitrophenylhydrazine):** - Both aldehydes and ketones form a yellow/orange/red precipitate. - While it does not distinguish between the two alone, the reaction can be followed by another test for confirmation.
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