Synthesis of Benzoylamino Acids from Glycine, Alanine, and Valine Lab: The synth
ID: 858077 • Letter: S
Question
Synthesis of Benzoylamino Acids from Glycine, Alanine, and Valine Lab:The synthesis included the initial Amino Acid (Glycine, Alanine, & Valine), in addition to Benzoyl Chloride, then reacted with NaOH (aq) and HCl, to the produce the respective (R,S)-Benzoylamino Acid derivative products.
Questions: 1. Why is the benzoylamino product soluble in the aqueous reaction solution until HCl is added?
2. Why must NaOH be present for the reaction between an amino acid and benzoyl chloride to take place at a reasonable rate?
3. A possible alternative procedure would be to add all the 6 M NaOH solution at the beginning of the reaction. What disadvantage could this have? Synthesis of Benzoylamino Acids from Glycine, Alanine, and Valine Lab:
The synthesis included the initial Amino Acid (Glycine, Alanine, & Valine), in addition to Benzoyl Chloride, then reacted with NaOH (aq) and HCl, to the produce the respective (R,S)-Benzoylamino Acid derivative products.
Questions: 1. Why is the benzoylamino product soluble in the aqueous reaction solution until HCl is added?
2. Why must NaOH be present for the reaction between an amino acid and benzoyl chloride to take place at a reasonable rate?
3. A possible alternative procedure would be to add all the 6 M NaOH solution at the beginning of the reaction. What disadvantage could this have?
The synthesis included the initial Amino Acid (Glycine, Alanine, & Valine), in addition to Benzoyl Chloride, then reacted with NaOH (aq) and HCl, to the produce the respective (R,S)-Benzoylamino Acid derivative products.
Questions: 1. Why is the benzoylamino product soluble in the aqueous reaction solution until HCl is added?
2. Why must NaOH be present for the reaction between an amino acid and benzoyl chloride to take place at a reasonable rate?
3. A possible alternative procedure would be to add all the 6 M NaOH solution at the beginning of the reaction. What disadvantage could this have?
Explanation / Answer
a) the benzoylamino product is soluble in aqeous solution as it is in the form of sodium salt. The salt is soluble in water. However on addition of HCl it gets converted to carboxylic acid hence becomes insolulbe in aqeous medium
b) NaOH is used to consume the H+ generated by reactio of each benzoyl chloride with glcyine. So NaOH consumes the proton. WE need glycine in anionic form, so H+ should be consumed
c) If we will use excess of NaOH in the beginning of reaction then it will cause unwanted reaction of NaOH with Benzoyl peroxide and smell in the reaction.
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