Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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**alanine structure: NH2-(CH3)-CH-(COOH)**
2. The structure of ascorbic acid is shown below. Redraw the structure on your sheet of paper and circle the most acidic hydrogen. Briefly explain your selection.
**ascorbic acid structure: C6H8O6**
**Explanations:**
1. **Alanine**:
- **Most Acidic Site**: The carboxyl group (-COOH) is the most acidic site in the molecule due to its ability to donate a proton (H+).
- **Most Basic Site**: The amino group (-NH2) is the most basic site because it can accept a proton.
- **Reaction with Sodium Hydroxide (NaOH)**:
- When alanine reacts with NaOH, the carboxyl group loses a hydrogen ion (H+), forming a carboxylate anion (-COO^-).
- Structure after reaction: NH2-(CH3)-CH-(COO^-Na+)
- **Reaction with Hydrochloric Acid (HCl)**:
- When alanine reacts with HCl, the amino group gains a hydrogen ion (H+), forming an ammonium ion (-NH3+).
- Structure after reaction: NH3+-(CH3)-CH-(COOH)
2. **Ascorbic Acid**:
- You are required to redraw the structure of ascorbic acid and circle the most acidic hydrogen (usually the hydrogen attached to an oxygen in a hydroxyl group adjacent to a double-bonded oxygen in ascorbic acid, due to resonance stabilization of the resulting anion).
These exercises help in understanding the acid-base properties of organic compounds and predicting the outcome of chemical reactions.](https://content.bartleby.com/qna-images/question/c2ac78f1-4bd5-465a-a046-ce4666415bd3/1b131356-fd03-4da6-95e4-c7458e0a7aa5/mwrx1ox_processed.jpeg)
Transcribed Image Text:**Chemistry Problem Set: Understanding Acid-Base Properties in Organic Molecules**
1. The structure of the amino acid alanine is shown below:
i. Identify the most acidic and most basic sites in the molecule.
ii. Draw the structure of the product formed by treating alanine with one equivalent of sodium hydroxide.
iii. Draw the structure of the product formed by treating alanine with one equivalent of hydrochloric acid.
**alanine structure: NH2-(CH3)-CH-(COOH)**
2. The structure of ascorbic acid is shown below. Redraw the structure on your sheet of paper and circle the most acidic hydrogen. Briefly explain your selection.
**ascorbic acid structure: C6H8O6**
**Explanations:**
1. **Alanine**:
- **Most Acidic Site**: The carboxyl group (-COOH) is the most acidic site in the molecule due to its ability to donate a proton (H+).
- **Most Basic Site**: The amino group (-NH2) is the most basic site because it can accept a proton.
- **Reaction with Sodium Hydroxide (NaOH)**:
- When alanine reacts with NaOH, the carboxyl group loses a hydrogen ion (H+), forming a carboxylate anion (-COO^-).
- Structure after reaction: NH2-(CH3)-CH-(COO^-Na+)
- **Reaction with Hydrochloric Acid (HCl)**:
- When alanine reacts with HCl, the amino group gains a hydrogen ion (H+), forming an ammonium ion (-NH3+).
- Structure after reaction: NH3+-(CH3)-CH-(COOH)
2. **Ascorbic Acid**:
- You are required to redraw the structure of ascorbic acid and circle the most acidic hydrogen (usually the hydrogen attached to an oxygen in a hydroxyl group adjacent to a double-bonded oxygen in ascorbic acid, due to resonance stabilization of the resulting anion).
These exercises help in understanding the acid-base properties of organic compounds and predicting the outcome of chemical reactions.
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