. Fill in the mechanism below with curved-arrow electron pushing as well as necessary lone pairs of electrons and all formal charges. Note: Some atoms are only shown when relevant.   b. Circle the rate determining step of the reaction.

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...
icon
Related questions
icon
Concept explainers
Question

a. Fill in the mechanism below with curved-arrow electron pushing as well as necessary lone pairs of electrons and all formal charges. Note: Some atoms are only shown when relevant.

 

b. Circle the rate determining step of the reaction.

### Mechanism of Alcohol Conversion to Alkyl Chloride using Hydrochloric Acid

The image outlines the detailed step-by-step mechanism of converting an alcohol group to an alkyl chloride using hydrochloric acid (HCl). The chemical reaction progresses through several stages, incorporating the protonation of the alcohol group and subsequent substitution of the water molecule with a chloride ion (Cl-).

#### Step-by-Step Mechanism:

1. **Protonation of Alcohol:**
   - Initially, the alcohol (ROH) is protonated by hydrochloric acid (HCl), resulting in the formation of an oxonium ion (ROH2+).

   \[
   \text{Alcohol (\(ROH\))} + HCl \rightarrow \text{Protonated Alcohol (\(ROH_2^+\))}
   \]

   ![Chemical Reaction](image)
  
2. **Formation of Carbocation Intermediate:**
   - The protonated alcohol (ROH2+) loses a water molecule (H2O) to form a carbocation (R+). This is indicated by the departure of the water molecule.

   \[
   \text{Protonated Alcohol (\(ROH_2^+\))} \rightarrow \text{Carbocation (\(R^+\))} + H_2O
   \]

   ![Chemical Reaction](image)

3. **Nucleophilic Attack by Chloride Ion:**
   - The chloride ion (Cl-) then attacks the carbocation, leading to the formation of alkyl chloride (RCl).

   \[
   \text{Carbocation (\(R^+\))} + Cl^- \rightarrow \text{Alkyl Chloride (\(RCl\))}
   \]

   ![Chemical Reaction](image)

### Detailed Example:
The diagram illustrates specific molecular structures undergoing the described transformation. The initial reactant, an alcohol, is progressively converted into an alkyl chloride.

1. **Starting Alcohol:**
   The reactant is a simple alcohol, depicted with its hydroxyl group (OH).

2. **Protonation:**
   Upon treatment with hydrochloric acid, the hydroxyl group is protonated, forming an oxonium ion (indicated by a positively charged oxygen attached to two hydrogens).

3. **Formation of Carbocation:**
   The intermediate oxonium ion releases a water molecule, resulting in a positively charged carbon structure or carbocation.

4.
Transcribed Image Text:### Mechanism of Alcohol Conversion to Alkyl Chloride using Hydrochloric Acid The image outlines the detailed step-by-step mechanism of converting an alcohol group to an alkyl chloride using hydrochloric acid (HCl). The chemical reaction progresses through several stages, incorporating the protonation of the alcohol group and subsequent substitution of the water molecule with a chloride ion (Cl-). #### Step-by-Step Mechanism: 1. **Protonation of Alcohol:** - Initially, the alcohol (ROH) is protonated by hydrochloric acid (HCl), resulting in the formation of an oxonium ion (ROH2+). \[ \text{Alcohol (\(ROH\))} + HCl \rightarrow \text{Protonated Alcohol (\(ROH_2^+\))} \] ![Chemical Reaction](image) 2. **Formation of Carbocation Intermediate:** - The protonated alcohol (ROH2+) loses a water molecule (H2O) to form a carbocation (R+). This is indicated by the departure of the water molecule. \[ \text{Protonated Alcohol (\(ROH_2^+\))} \rightarrow \text{Carbocation (\(R^+\))} + H_2O \] ![Chemical Reaction](image) 3. **Nucleophilic Attack by Chloride Ion:** - The chloride ion (Cl-) then attacks the carbocation, leading to the formation of alkyl chloride (RCl). \[ \text{Carbocation (\(R^+\))} + Cl^- \rightarrow \text{Alkyl Chloride (\(RCl\))} \] ![Chemical Reaction](image) ### Detailed Example: The diagram illustrates specific molecular structures undergoing the described transformation. The initial reactant, an alcohol, is progressively converted into an alkyl chloride. 1. **Starting Alcohol:** The reactant is a simple alcohol, depicted with its hydroxyl group (OH). 2. **Protonation:** Upon treatment with hydrochloric acid, the hydroxyl group is protonated, forming an oxonium ion (indicated by a positively charged oxygen attached to two hydrogens). 3. **Formation of Carbocation:** The intermediate oxonium ion releases a water molecule, resulting in a positively charged carbon structure or carbocation. 4.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 4 steps with 1 images

Blurred answer
Knowledge Booster
Basics in Organic Reaction Mechanisms
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY