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青州's Question
Chemistry
Posted 9 months ago

8 Question: In a challenging laboratory experiment, an organic chemist synthesizes a novel compound "Alpha" with a molecular formula of C9H10O2\mathrm{C}_{9} \mathrm{H}_{10} \mathrm{O}_{2}. When "Alpha" is treated with sodium...
In a challenging laboratory experiment, an organic chemist synthesizes a novel compound "Alpha" with a molecular formula of C9H10O2\mathrm{C}_{9} \mathrm{H}_{10} \mathrm{O}_{2}. When "Alpha" is treated with sodium borohydride (NaBH4)\left(\mathrm{NaBH}_{4}\right), it yields a compound "Beta" with a molecular formula C9\mathrm{C}_{9} H12O2\mathrm{H}_{12} \mathrm{O}_{2}. Further, "Beta" reacts with acidified potassium permanganate (KMnO4/H+)\left(\mathrm{KMnO}_{4} / \mathrm{H}^{+}\right)to form a compound "Gamma" (C9H12O3)\left(\mathrm{C}_{9} \mathrm{H}_{12} \mathrm{O}_{3}\right). Determine the structures of compounds Alpha, Beta, and Gamma, and explain the type of chemical reactions involved in each transformation.
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Answer from Sia
Posted 9 months ago
Solution
1
Identify the reaction: The molecular formula of "Alpha" is C9H10O2C_9H_{10}O_2. When treated with sodium borohydride (NaBH4NaBH_4), it yields "Beta" with a molecular formula C9H12O2C_9H_{12}O_2. This indicates a reduction reaction where NaBH4NaBH_4 reduces a carbonyl group (likely an aldehyde or ketone) to an alcohol
2
Determine the structure of "Alpha": Given the molecular formula C9H10O2C_9H_{10}O_2 and the reduction reaction, "Alpha" likely contains a carbonyl group. A plausible structure is a benzene ring with a formyl group (aldehyde) and a methoxy group, such as 4-methoxybenzaldehyde
3
Identify the reaction for "Beta": The molecular formula of "Beta" is C9H12O2C_9H_{12}O_2. This suggests that the aldehyde group in "Alpha" has been reduced to a primary alcohol, resulting in 4-methoxybenzyl alcohol
4
Determine the structure of "Beta": Based on the reduction, "Beta" is likely 4-methoxybenzyl alcohol (C9H12O2C_9H_{12}O_2)
5
Identify the reaction for "Gamma": "Beta" reacts with acidified potassium permanganate (KMnO4/H+KMnO_4 / H^+) to form "Gamma" with a molecular formula C9H12O3C_9H_{12}O_3. This indicates an oxidation reaction where the primary alcohol is oxidized to a carboxylic acid
6
Determine the structure of "Gamma": Based on the oxidation, "Gamma" is likely 4-methoxybenzoic acid (C9H12O3C_9H_{12}O_3)
Answer
The structures of the compounds are as follows: - "Alpha": 4-methoxybenzaldehyde (C9H10O2C_9H_{10}O_2) - "Beta": 4-methoxybenzyl alcohol (C9H12O2C_9H_{12}O_2) - "Gamma": 4-methoxybenzoic acid (C9H12O3C_9H_{12}O_3)
Key Concept
Reduction and oxidation reactions in organic chemistry
Explanation
Sodium borohydride (NaBH4NaBH_4) is a reducing agent that converts aldehydes to primary alcohols, while acidified potassium permanganate (KMnO4/H+KMnO_4 / H^+) is an oxidizing agent that converts primary alcohols to carboxylic acids.

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