1. Complete the following outlined reactions that begin with propanoic acid. NaOH(aq) он NH3 2 eq + benzyl alcohol Гон SOCI, Li[(BuO),AIH] Na* `NH2 2 eq
1. Complete the following outlined reactions that begin with propanoic acid. NaOH(aq) он NH3 2 eq + benzyl alcohol Гон SOCI, Li[(BuO),AIH] Na* `NH2 2 eq
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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![**Outline of Organic Reactions Starting from Propanoic Acid**
This educational section focuses on a series of chemical reactions that begin with propanoic acid. Below we provide a step-by-step guide through the reactions, including reagents and intermediates, leading to the final products.
1. Starting Compound: **Propanoic Acid (C₃H₆O₂)**
**Step-by-Step Reaction Details:**
1. Propanoic acid undergoes a reaction with thionyl chloride (SOCl₂).
- **Reagents:** SOCl₂ (thionyl chloride)
- **Product:** Propanoyl chloride (an acyl chloride)
2. Propanoyl chloride reacts with ammonia (NH₃).
- **Reagents:** NH₃ (2 equivalents)
- **Product:** Propanamide
3. Propanamide reacts with benzyl alcohol.
- **Reagents:** Benzyl alcohol
- **Intermediate:** Carboxylic acid (produced from the reaction of benzyl alcohol and propanamide)
4. Propanamide also undergoes further reduction with lithium tri-tert-butoxyaluminium hydride (Li[(t-BuO)₃AlH]).
- **Reagents:** Li[(t-BuO)₃AlH]
- **Products:** Reduced amides to produce an amine
5. The conversion of this amine using ethylamine (CH₃CH₂NH₂) in two equivalents yields another intermediate product.
- **Reagents:** Ethylamine (2 equivalents)
- **Product:** New amine structure
6. The new amine undergoes hydrolysis with aqueous NaOH (sodium hydroxide).
- **Reagents:** NaOH (aqueous)
- **Product:** Benzyl alcohol
**Graphical Representation of the Reaction Sequence:**
- **First Diagram:** Introduction of propanoic acid (C₃H₆O₂) with SOCl₂ producing an acyl chloride.
- **Second Diagram:** Acyl chloride interaction with NH₃ to form propanamide.
- **Third Diagram:** Benzyl alcohol reacting with propanamide leading to a carboxylic acid intermediate.
- **Fourth Diagram:** Reduction of propanamide using Li[(t-BuO)₃AlH] to produce an amine.
- **Fifth Diagram:** Reacting the am](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fff015db4-0da8-42fc-9d60-01a672218c35%2F78ab82c1-2d2f-424d-933b-1d06a95789ce%2F0541cf_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Outline of Organic Reactions Starting from Propanoic Acid**
This educational section focuses on a series of chemical reactions that begin with propanoic acid. Below we provide a step-by-step guide through the reactions, including reagents and intermediates, leading to the final products.
1. Starting Compound: **Propanoic Acid (C₃H₆O₂)**
**Step-by-Step Reaction Details:**
1. Propanoic acid undergoes a reaction with thionyl chloride (SOCl₂).
- **Reagents:** SOCl₂ (thionyl chloride)
- **Product:** Propanoyl chloride (an acyl chloride)
2. Propanoyl chloride reacts with ammonia (NH₃).
- **Reagents:** NH₃ (2 equivalents)
- **Product:** Propanamide
3. Propanamide reacts with benzyl alcohol.
- **Reagents:** Benzyl alcohol
- **Intermediate:** Carboxylic acid (produced from the reaction of benzyl alcohol and propanamide)
4. Propanamide also undergoes further reduction with lithium tri-tert-butoxyaluminium hydride (Li[(t-BuO)₃AlH]).
- **Reagents:** Li[(t-BuO)₃AlH]
- **Products:** Reduced amides to produce an amine
5. The conversion of this amine using ethylamine (CH₃CH₂NH₂) in two equivalents yields another intermediate product.
- **Reagents:** Ethylamine (2 equivalents)
- **Product:** New amine structure
6. The new amine undergoes hydrolysis with aqueous NaOH (sodium hydroxide).
- **Reagents:** NaOH (aqueous)
- **Product:** Benzyl alcohol
**Graphical Representation of the Reaction Sequence:**
- **First Diagram:** Introduction of propanoic acid (C₃H₆O₂) with SOCl₂ producing an acyl chloride.
- **Second Diagram:** Acyl chloride interaction with NH₃ to form propanamide.
- **Third Diagram:** Benzyl alcohol reacting with propanamide leading to a carboxylic acid intermediate.
- **Fourth Diagram:** Reduction of propanamide using Li[(t-BuO)₃AlH] to produce an amine.
- **Fifth Diagram:** Reacting the am
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