**Title: Analyzing Organic Compounds Using Various Tests****Introduction:**This educational module focuses on analyzing specific organic compounds through chemical tests and reactions, such as Tollens' test, oxidation, reduction, solubility, and NMR spectroscopy. **Compounds:**- **A:** \( \text{(CH}_3\text{O)}_2\text{C=O} \) - **B:** \( \text{Benzaldehyde (C}_6\text{H}_5\text{CHO)} \)- **C:** \( \text{Cyclohexanone (C}_6\text{H}_{10}\text{O)} \)- **D:** \( \text{Ethanol (HOCH}_2\text{CH}_3) \)- **E:** \( \text{Styrene (C}_8\text{H}_8) \)- **F:** \( \text{Phenethyl alcohol (C}_8\text{H}_{10}\text{O)} \)**Questions and Answers:**a) **Which one(s) would give a positive Tollens' (silver mirror) test?** - **Answer:** Ab) **Which one(s) could be oxidized with CrO3?** - **Answer:** Dc) **Which one(s) could be reduced with NaBH4?** - **Answer:** A, Cd) **Which one(s) would dissolve in water?** - **Answer:** De) **Which one(s) would have a peak in the 'H NMR spectrum which would disappear when D2O is added?** - **Answer:** B**Discussion:**1. **Tollens' Test:** - A Tollens' test is used to identify aldehydes. Compound A contains an acetal group that can potentially react under these conditions.2. **Oxidation with CrO3:** - Ethanol (D) can be oxidized to an aldehyde or carboxylic acid.3. **Reduction with NaBH4:** - Both ketones (C) and certain esters/aldehydes (A) can be reduced by sodium borohydride.4. **Solubility in Water:** - Ethanol (D) is soluble in water due

Answered: A= Consider the following compounds…

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: Analyzing Organic Compounds Using Various Tests**

**Introduction:**
This educational module focuses on analyzing specific organic compounds through chemical tests and reactions, such as Tollens' test, oxidation, reduction, solubility, and NMR spectroscopy.

**Compounds:**
- **A:** \( \text{(CH}_3\text{O)}_2\text{C=O} \)
- **B:** \( \text{Benzaldehyde (C}_6\text{H}_5\text{CHO)} \)
- **C:** \( \text{Cyclohexanone (C}_6\text{H}_{10}\text{O)} \)
- **D:** \( \text{Ethanol (HOCH}_2\text{CH}_3) \)
- **E:** \( \text{Styrene (C}_8\text{H}_8) \)
- **F:** \( \text{Phenethyl alcohol (C}_8\text{H}_{10}\text{O)} \)

**Questions and Answers:**

a) **Which one(s) would give a positive Tollens' (silver mirror) test?**
- **Answer:** A

b) **Which one(s) could be oxidized with CrO3?**
- **Answer:** D

c) **Which one(s) could be reduced with NaBH4?**
- **Answer:** A, C

d) **Which one(s) would dissolve in water?**
- **Answer:** D

e) **Which one(s) would have a peak in the 'H NMR spectrum which would disappear when D2O is added?**
- **Answer:** B

**Discussion:**
1. **Tollens' Test:**
- A Tollens' test is used to identify aldehydes. Compound A contains an acetal group that can potentially react under these conditions.

2. **Oxidation with CrO3:**
- Ethanol (D) can be oxidized to an aldehyde or carboxylic acid.

3. **Reduction with NaBH4:**
- Both ketones (C) and certain esters/aldehydes (A) can be reduced by sodium borohydride.

4. **Solubility in Water:**
- Ethanol (D) is soluble in water due

Expert Solution

Step 1

a) Tollen's test is given by compounds which have aldehyde groups. Out here, the compound A has a aldehydic CHO group.

b) Oxidation with CrO₃ converts alcohol to aldehyde/ketone. C and D are alcohol. But C cannot be oxidised as it has no Hydrogen. So, only D can be oxidised.

c) C=O can be reduced with NaBH4, only aldehyde and ketone, not ester group. So, B cannot be reduced but A and E can be.

d) Alcohols readily dissolve in water as they can form hydrogen bonding. So, C and D

e) On adding D₂O, tautomerism can occur and the Hydrogen at the alpha position can be exchanged with deuterium. So, a ¹HNMR peak will disappear. Option E is correct.

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