Textbook Question
Draw the products of the following reactions: b. pentanoic acid + PBr3 + Br2, followed by hydrolysis
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- 1. A Review of General Chemistry5h 5m
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- Intro to Citric Acid Cycle7m
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- 34. Nucleic Acids1h 32m
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- 36. Synthetic Polymers1h 49m
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24. Enolate Chemistry: Reactions at the Alpha-Carbon
Hell-Volhard-Zelinski Reaction
Struggling with Organic Chemistry?
Join thousands of students who trust us to help them ace their exams!Watch the first videoMultiple Choice
Provide the major product after each step for the following reaction.
A
B
C
D
Verified step by step guidance1
Identify the starting material as a carboxylic acid with a ketone group, specifically 2-oxopropanoic acid.
The first step involves the reaction with Br2 and PBr3. This is a Hell-Volhard-Zelinsky (HVZ) reaction, which brominates the alpha position of the carboxylic acid. The PBr3 converts the carboxylic acid to an acyl bromide, which facilitates the alpha bromination.
After bromination, water is used to hydrolyze the acyl bromide back to the carboxylic acid, but with a bromine atom at the alpha position.
In the second step, the alpha-bromo acid reacts with NH3 (ammonia). This is a nucleophilic substitution reaction where the bromine is replaced by an amino group, resulting in an alpha-amino acid.
The final product is an alpha-amino acid, specifically 2-aminopropanoic acid, which is also known as alanine.
Related Practice
Hell-Volhard-Zelinski Reaction practice set
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