Alcohols Phenols and EthershardMCQ SINGLE

See imageAlcohols Phenols and Ethers Chemistry Question

Question

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Chemistry diagram for: See image
Answer: C

💡 Solution & Explanation

Step 1: Identify succinic acid. Succinic acid is HOOC-CH2-CH2-COOH (a dicarboxylic acid with 4 carbons). Step 2: Succinic acid --Delta--> (A). When succinic acid is heated, it undergoes intramolecular dehydration (since the two carboxyl groups are 1,4-related and can form a 5-membered ring) to give succinic anhydride (a cyclic anhydride). Step 3: Succinic anhydride --NH3/Delta--> (B). When succinic anhydride reacts with ammonia and is heated, it first forms the ammonium salt, then loses water upon heating to give succinimide (the cyclic imide: a 5-membered ring with -CO-NH-CO- and -CH2-CH2- bridging). Step 4: Succinimide --Br2/KOH--> (C). This is the Hofmann bromamide degradation (Hofmann rearrangement) applied to an imide. In the Hofmann rearrangement, an amide (or imide) reacts with Br2/KOH to give an amine with one fewer carbon. For succinimide (cyclic imide with two carbonyl groups flanking nitrogen), the Hofmann degradation converts one of the amide carbonyls: the ring opens and one -CO- group is lost as CO2, giving beta-alanine (3-aminopropionic acid): H2N-CH2-CH2-COOH, i.e., NH2-CH2-CH2-CO2H. However, examining the options more carefully: option (c) is CH2-CO2^- K^+ | CH2-NH2, which represents the potassium salt of beta-alanine (since KOH is used in the reaction medium, the carboxylate would be deprotonated to give the potassium carboxylate salt). The product formed in Br2/KOH conditions is the amine in basic (KOH) medium, so the carboxylic acid group would be deprotonated to give -CO2^- K^+, and the amine is -NH2. This matches option (c): the potassium salt of beta-alanine: K^+^-OOC-CH2-CH2-NH2. Option (b) would require only a 2-carbon chain (glycine analog), which is inconsistent. Option (a) has a 4-carbon chain with terminal amine, inconsistent. Option (d) shows bromination product, not Hofmann product. Why other options fail: - (a): Shows a 4-carbon aminoacid (beta-aminobutyric acid analog) - wrong carbon count from Hofmann on succinimide. - (b): Shows only 2 carbons (glycine-like structure) - wrong, succinimide Hofmann gives 3-carbon product. - (d): Shows a brominated product, not the Hofmann rearrangement amine product. Therefore, the correct answer is C.

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