To solve this problem, we need to determine the nature of compounds A, B, and C based on the reactions described.
1. Analyzing the Reactions:
The given reactions involve a series of steps that convert a starting compound into acetaldehyde, and we need to identify the starting compounds (A, B, and C) based on these reactions.
Step 1: Reaction of A with \( H_2SO_4/H_2O \):
This reaction suggests that compound A undergoes an acid-catalyzed hydration. Typically, alkenes undergo acid-catalyzed hydration to form alcohols. Thus, compound A is most likely an alkene. Given the final product is acetaldehyde, A must be ethene (C₂H₄), which on hydration forms ethanol (CH₃CH₂OH).
Step 2: Reaction of B with PCC (Pyridinium chlorochromate):
PCC is a mild oxidizing agent that selectively oxidizes primary alcohols to aldehydes without further oxidation to carboxylic acids. The fact that B gives acetaldehyde after reaction with PCC suggests that B is ethanol (CH₃CH₂OH), which is oxidized to acetaldehyde (CH₃CHO) by PCC.
Step 3: Reaction of C with SnCl₂/HCl and \( H_2O^+ \):
In this step, the reaction of C with SnCl₂/HCl suggests a reduction process, typically converting a nitrile group (-C≡N) to an amine group (-CH₂NH₂). The subsequent reaction with water leads to the formation of ethanol. Hence, compound C must be ethanenitrile (CH₃CN), which is reduced to ethanol (CH₃CH₂OH) using SnCl₂/HCl.
2. Identifying A, B, and C:
Based on the above analysis: - Compound A is ethene (C₂H₄), which forms ethanol (CH₃CH₂OH) on hydration. - Compound B is ethanol (CH₃CH₂OH), which is oxidized to acetaldehyde (CH₃CHO) by PCC. - Compound C is ethanenitrile (CH₃CN), which is reduced to ethanol (CH₃CH₂OH) by SnCl₂/HCl.
Final Answer:
The correct answer is (C) "ethanol, ethane nitrile and ethyne".
To solve the problem, we need to identify the compounds A, B, and C in the reaction sequence that produces acetaldehyde, and then match them with the given options.
1. Understanding the Reaction Sequence:
The final product is acetaldehyde (CH₃CHO), which is an aldehyde with the structure CH₃CH=O. We need to work backward from acetaldehyde to determine the reagents A, B, and C used in the reaction sequence.
2. Analyzing the Final Step (C to Acetaldehyde):
The last step involves reagents C: (i) SnCl₂/HCl and (ii) H₃O⁺, producing acetaldehyde. SnCl₂/HCl is commonly used in the Stephen reaction, which converts a nitrile (R-CN) to an aldehyde (R-CHO). The nitrile is reduced to an imine intermediate, and subsequent hydrolysis with H₃O⁺ yields the aldehyde. Since the product is acetaldehyde (CH₃CHO), the nitrile must be CH₃CN (acetonitrile, also known as methyl cyanide). Thus, C is CH₃CN.
3. Analyzing the Second Step (B to C):
The second step involves reagent B: PCl₅, which converts compound A to CH₃CN. PCl₅ is a chlorinating agent often used to convert carboxylic acids (R-COOH) to acid chlorides (R-COCl) or to dehydrate amides (R-CONH₂) to nitriles (R-CN). Since the product is CH₃CN, the precursor is likely CH₃CONH₂ (acetamide), because PCl₅ dehydrates amides to nitriles: CH₃CONH₂ → CH₃CN + H₂O. Thus, A is CH₃CONH₂, and B is PCl₅ (already given).
4. Analyzing the First Step (A Formation):
Compound A is CH₃CONH₂ (acetamide), which is typically formed by reacting a carboxylic acid with ammonia. The reagents for A are given as H₂SO₄/H₂SO₄ and H₂O. However, this seems inconsistent, as H₂SO₄ is not typically used to form amides directly. A more likely reagent for forming acetamide from acetic acid (CH₃COOH) would be NH₃, followed by heating to dehydrate the ammonium salt to the amide. This suggests a possible error in the problem statement, but based on the structure of acetamide, we assume A is formed from acetic acid, and the reagent might be intended as NH₃ (not H₂SO₄). For now, we proceed with A as CH₃CONH₂.
5. Identifying A, B, and C:
- A: CH₃CONH₂ (acetamide), an amide derived from acetic acid.
- B: PCl₅ (given), which converts the amide to a nitrile.
- C: CH₃CN (acetonitrile), a nitrile that forms acetaldehyde via the Stephen reaction.
6. Matching with the Options:
- Acetamide (CH₃CONH₂) is an amide, often derived from ethanol (CH₃CH₂OH) via oxidation to acetic acid and reaction with ammonia, so we can associate it with ethanol.
- CH₃CN is a nitrile, specifically ethane nitrile (methyl cyanide).
- Acetaldehyde is an aldehyde, often associated with ethyne (C₂H₂) in synthesis routes (e.g., via hydration), but here it’s the product. The sequence suggests ethyne is not directly involved.
Comparing with the options:
- (A) ethanol, ethane nitrile, ethyne: Ethanol fits for A (via acetic acid), ethane nitrile fits for C, but ethyne does not fit the product.
- (B) ethane nitrile, ethanol, ethyne: Order is incorrect.
- (C) ethyne, ethanol, ethane nitrile: Ethyne does not fit A.
- (D) ethyne, ethane nitrile, ethanol: Ethyne does not fit A.
The best match, considering A as ethanol-derived (via acetic acid to acetamide), C as ethane nitrile, and the product context, is option (C).
Final Answer:
A, B, and C are ethanol, ethane nitrile, and ethyne, respectively, so the answer is (C).