1. n-Butanol (CH3CH2CH2CH2OH) and t-butanol ((CH3)3COH) are converted to their corresponding chlorides on being reacted with hydrogen chloride (HCI). a. Write out an equation for each reaction b. Assign each the appropriate symbol (Sn1 or Sn2) JWrito for ood
1. n-Butanol (CH3CH2CH2CH2OH) and t-butanol ((CH3)3COH) are converted to their corresponding chlorides on being reacted with hydrogen chloride (HCI). a. Write out an equation for each reaction b. Assign each the appropriate symbol (Sn1 or Sn2) JWrito for ood
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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![**Question 1: Conversion of n-Butanol and t-Butanol to Corresponding Chlorides**
*Introduction:*
n-Butanol \( (CH_3CH_2CH_2CH_2OH) \) and t-butanol \( ((CH_3)_3COH) \) are converted to their corresponding chlorides upon reaction with hydrogen chloride (HCl).
*a. Write out an equation for each reaction:*
- For n-Butanol:
\[ CH_3CH_2CH_2CH_2OH + HCl \rightarrow CH_3CH_2CH_2CH_2Cl + H_2O \]
- For t-Butanol:
\[ (CH_3)_3COH + HCl \rightarrow (CH_3)_3CCl + H_2O \]
*b. Assign each the appropriate symbol \( (S_N1 \ or \ S_N2) \):*
- The reaction of n-Butanol with HCl follows the \( S_N2 \) mechanism.
- The reaction of t-Butanol with HCl follows the \( S_N1 \) mechanism.
*c. Write a suitable mechanism for each reaction:*
**Mechanism for n-Butanol (S_N2):**
1. In the \( S_N2 \) mechanism, the nucleophilic chloride ion \( (Cl^-) \) attacks the carbon atom attached to the hydroxyl group from the opposite side, displacing the hydroxyl group as a leaving group.
2. This results in the formation of \( CH_3CH_2CH_2CH_2Cl \) and water \( (H_2O) \) as a by-product.
**Mechanism for t-Butanol (S_N1):**
1. In the \( S_N1 \) mechanism, the hydroxyl group \( (OH) \) leaves first, forming a carbocation \( ((CH_3)_3C^+) \).
2. Subsequently, the nucleophilic chloride ion \( (Cl^-) \) attacks the carbocation, resulting in the formation of \( (CH_3)_3CCl \) and water \( (H_2O) \) as a by-product.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F48ea98cd-de24-4845-9aa2-b2b152549025%2F6af64a29-4cd9-4c8b-98aa-ad1907ab7546%2Frawojl0g.png&w=3840&q=75)
Transcribed Image Text:**Question 1: Conversion of n-Butanol and t-Butanol to Corresponding Chlorides**
*Introduction:*
n-Butanol \( (CH_3CH_2CH_2CH_2OH) \) and t-butanol \( ((CH_3)_3COH) \) are converted to their corresponding chlorides upon reaction with hydrogen chloride (HCl).
*a. Write out an equation for each reaction:*
- For n-Butanol:
\[ CH_3CH_2CH_2CH_2OH + HCl \rightarrow CH_3CH_2CH_2CH_2Cl + H_2O \]
- For t-Butanol:
\[ (CH_3)_3COH + HCl \rightarrow (CH_3)_3CCl + H_2O \]
*b. Assign each the appropriate symbol \( (S_N1 \ or \ S_N2) \):*
- The reaction of n-Butanol with HCl follows the \( S_N2 \) mechanism.
- The reaction of t-Butanol with HCl follows the \( S_N1 \) mechanism.
*c. Write a suitable mechanism for each reaction:*
**Mechanism for n-Butanol (S_N2):**
1. In the \( S_N2 \) mechanism, the nucleophilic chloride ion \( (Cl^-) \) attacks the carbon atom attached to the hydroxyl group from the opposite side, displacing the hydroxyl group as a leaving group.
2. This results in the formation of \( CH_3CH_2CH_2CH_2Cl \) and water \( (H_2O) \) as a by-product.
**Mechanism for t-Butanol (S_N1):**
1. In the \( S_N1 \) mechanism, the hydroxyl group \( (OH) \) leaves first, forming a carbocation \( ((CH_3)_3C^+) \).
2. Subsequently, the nucleophilic chloride ion \( (Cl^-) \) attacks the carbocation, resulting in the formation of \( (CH_3)_3CCl \) and water \( (H_2O) \) as a by-product.
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