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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![**Problem 2: Synthesizing Alcohols Using Grignard Reagents**
**Task**: Propose two different methods to synthesize each of the following alcohols using a Grignard reagent.
**Model Example**:
- Target Alcohol: Butan-2-ol (CH₃CH₂CHOHCH₃)
**Method 1**:
1. React propanal (CH₃CH₂CHO) with methylmagnesium bromide (CH₃MgBr).
2. Perform acidic work-up using hydronium ion (H₃O⁺).
**Method 2**:
1. React acetaldehyde (CH₃CHO) with butylmagnesium bromide (CH₃CH₂CH₂CH₂MgBr).
2. Perform acidic work-up using hydronium ion (H₃O⁺).
**Target Alcohols**:
a. **Alcohol Structure**:
\[
\text{OH positioned on a cyclopentane with two ethyl groups.}
\]
b. **Alcohol Structure**:
\[
\text{OH on a hexane chain with methyl branching at the third carbon.}
\]
c. **Alcohol Structure**:
\[
\text{OH positioned on a cyclohexane with a methyl group.}
\]
**Instructions**: For each structure (a, b, c), outline two synthetic routes using different Grignard reagents and aldehyde or ketone starting materials, followed by an acidic work-up.
**Note**: Grignard reagents are organomagnesium compounds (RMgX) that add to carbonyl compounds, forming alcohols after hydrolysis. Please ensure safety when handling these reagents.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F04b28093-4f77-4d69-adb9-9e4a8e9f1bf0%2F95b7f8bc-faef-443e-a87c-202ebcba660a%2Fmjqqbvf_processed.jpeg&w=3840&q=75)
Transcribed Image Text:**Problem 2: Synthesizing Alcohols Using Grignard Reagents**
**Task**: Propose two different methods to synthesize each of the following alcohols using a Grignard reagent.
**Model Example**:
- Target Alcohol: Butan-2-ol (CH₃CH₂CHOHCH₃)
**Method 1**:
1. React propanal (CH₃CH₂CHO) with methylmagnesium bromide (CH₃MgBr).
2. Perform acidic work-up using hydronium ion (H₃O⁺).
**Method 2**:
1. React acetaldehyde (CH₃CHO) with butylmagnesium bromide (CH₃CH₂CH₂CH₂MgBr).
2. Perform acidic work-up using hydronium ion (H₃O⁺).
**Target Alcohols**:
a. **Alcohol Structure**:
\[
\text{OH positioned on a cyclopentane with two ethyl groups.}
\]
b. **Alcohol Structure**:
\[
\text{OH on a hexane chain with methyl branching at the third carbon.}
\]
c. **Alcohol Structure**:
\[
\text{OH positioned on a cyclohexane with a methyl group.}
\]
**Instructions**: For each structure (a, b, c), outline two synthetic routes using different Grignard reagents and aldehyde or ketone starting materials, followed by an acidic work-up.
**Note**: Grignard reagents are organomagnesium compounds (RMgX) that add to carbonyl compounds, forming alcohols after hydrolysis. Please ensure safety when handling these reagents.
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