Textbook Question
Predict the products of the following reactions.
(a) cyclopentyl methyl ketone + excess Cl2 + excess NaOH
(b) 1-cyclopentylethanol + excess I2 + excess NaOH
(c) propiophenone + excess Br2 + excess NaOH
24. Enolate Chemistry: Reactions at the Alpha-Carbon
Haloform Reaction
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Provide the major product for the following reaction.
A
B
C
D
Verified step by step guidance1
Identify the reaction type: The reaction involves a ketone with excess bromine (Br2) and sodium hydroxide (NaOH), which suggests a haloform reaction.
Understand the haloform reaction: This reaction occurs when a methyl ketone is treated with halogen and a base, leading to the formation of a carboxylate ion and a haloform (CHBr3 in this case).
Determine the structure of the starting material: The starting material is a methyl ketone, which is necessary for the haloform reaction to occur.
Predict the products: The methyl group adjacent to the carbonyl group will be converted into a carboxylate ion, and the remaining part of the molecule will form a carboxylic acid after acidification. The haloform (CHBr3) is also produced.
Consider the major product: The major organic product will be the carboxylic acid derived from the original ketone, and CHBr3 will be the byproduct.
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