Determine the mechanism of nucleophilic substitut a. Br + -CN acetone b. + -OCH3 C. + CH3OH Br H Br CH,CH,CH3 DMSO

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Title: **Nucleophilic Substitution Reaction Analysis**

**Objective:** 
Determine the mechanism of nucleophilic substitution for each reaction and draw the products, including stereochemistry.

**Reactions:**

1. **Reaction a:**
   \[
   \text{Reactants:} \quad \begin{aligned} 
   &\text{(CH3)CH-CH2-CH2Br} &+ \quad \overline{\text{CN}} \quad &\text{in acetone} 
   \end{aligned}
   \]
   \[
   \text{Products: \quad Secondary alkyl bromide substituted by CN group}
   \]

2. **Reaction b:**
   \[
   \text{Reactants:} \quad \begin{aligned} 
   &\text{(CH3)2CH-CHBrH} &+ \quad \overline{\text{OCH3}} \quad &\text{in DMSO}
   \end{aligned}
   \]
   \[
   \text{Products: \quad Alkyl bromide substituted by OCH3 group with inversion of stereochemistry.}
   \]

3. **Reaction c:**
   \[
   \text{Reactants:} \quad \begin{aligned} 
   &\text{Cyclohexane-Br with CH3CH2CH3 group} &+ \quad \text{CH3OH}
   \end{aligned}
   \]
   \[
   \text{Products: \quad Substitution of Br with OCH3 group in cyclohexane ring.}
   \]

4. **Reaction d:**
   \[
   \text{Reactants:} \quad \begin{aligned} 
   &\text{CH3CH3CH3C, I, H, CH3} &+ \quad \text{CH3COOH}
   \end{aligned}
   \]
   \[
   \text{Products: \quad Tertiary alkyl iodide substituted by COOCH3 group.}
   \]

5. **Reaction e:**
   \[
   \text{Reactants:} \quad \begin{aligned} 
   &\text{Cyclohexane-Br with CH3 group} &+ \quad \overline{\text{OCH2CH3}} \quad &
Transcribed Image Text:Title: **Nucleophilic Substitution Reaction Analysis** **Objective:** Determine the mechanism of nucleophilic substitution for each reaction and draw the products, including stereochemistry. **Reactions:** 1. **Reaction a:** \[ \text{Reactants:} \quad \begin{aligned} &\text{(CH3)CH-CH2-CH2Br} &+ \quad \overline{\text{CN}} \quad &\text{in acetone} \end{aligned} \] \[ \text{Products: \quad Secondary alkyl bromide substituted by CN group} \] 2. **Reaction b:** \[ \text{Reactants:} \quad \begin{aligned} &\text{(CH3)2CH-CHBrH} &+ \quad \overline{\text{OCH3}} \quad &\text{in DMSO} \end{aligned} \] \[ \text{Products: \quad Alkyl bromide substituted by OCH3 group with inversion of stereochemistry.} \] 3. **Reaction c:** \[ \text{Reactants:} \quad \begin{aligned} &\text{Cyclohexane-Br with CH3CH2CH3 group} &+ \quad \text{CH3OH} \end{aligned} \] \[ \text{Products: \quad Substitution of Br with OCH3 group in cyclohexane ring.} \] 4. **Reaction d:** \[ \text{Reactants:} \quad \begin{aligned} &\text{CH3CH3CH3C, I, H, CH3} &+ \quad \text{CH3COOH} \end{aligned} \] \[ \text{Products: \quad Tertiary alkyl iodide substituted by COOCH3 group.} \] 5. **Reaction e:** \[ \text{Reactants:} \quad \begin{aligned} &\text{Cyclohexane-Br with CH3 group} &+ \quad \overline{\text{OCH2CH3}} \quad &
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