the structure of the Product T is
This question involves identifying the structure of product T formed in a reaction sequence. The starting compound is a cyclic ketone with a bromine substituent, and it undergoes a specific reaction to form T. Based on the structure and typical reactions, this appears to be a case of Favorskii rearrangement.
Step 1: Recognize the Reaction
The given compound is 1-bromocyclopentanone. When treated with a base (like hydroxide ion), it undergoes Favorskii rearrangement. This reaction is characteristic of α-halo ketones (especially cyclic ones) and leads to ring contraction.
Step 2: Mechanism of Favorskii Rearrangement
The base deprotonates the α-carbon (if available), but in cyclic α-halo ketones, it often proceeds via formation of a cyclopropanone intermediate. The bromine is a good leaving group. The key steps are:
Step 3: Product Formation
Specifically, 1-bromocyclopentanone rearranges to cyclobutanecarboxylic acid. The reaction can be summarized as: So, for a 5-membered ring starting material, the product is a cyclobutanecarboxylic acid (4-membered ring).
Step 4: Identify Structure T
Among the options, look for cyclobutanecarboxylic acid. The correct structure is a cyclobutane ring with a carboxylic acid group (-COOH) attached.
Final Answer: The structure of T is cyclobutanecarboxylic acid, which corresponds to the option with a four-membered ring and -COOH group (you should compare the given images to identify this).
Favorskii Rearrangement: A reaction where α-halo ketones (especially cyclic) rearrange to carboxylic acids or esters with ring contraction. It involves a cyclopropanone intermediate and is base-catalyzed.
Ring Contraction Reactions: Chemical reactions that reduce the size of a cyclic compound, common in rearrangements like Favorskii.
Alpha-Halo Ketones: Compounds where a halogen is attached to the carbon adjacent to the carbonyl group; they are reactive and undergo various nucleophilic substitutions and rearrangements.
General Favorskii rearrangement for cyclic α-halo ketone: (n is the ring size; product has ring size n-1).