What is the major final product of the following reaction sequence? Only ane enantiomer of the possible products is shown. Br 1) H=K, NaH, THF 2) Na, NH3 (liq), t-BUOH 3) Cl2, CH,Cl, CI CI CI H CI H CI H CI

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If you can please go through the reaction steps and help me understand why it has the steriochemistry that it does?

**Title: Reaction Sequence and Stereochemistry**

**Question:**

What is the major final product of the following reaction sequence? Only one enantiomer of the possible products is shown.

**Reaction Sequence:**

1. Starting material: Benzyl bromide
2. Reagents and conditions:
   - 1) Sodium hydride (NaH), Tetrahydrofuran (THF)
   - 2) Sodium, Ammonia (liquid), tert-Butyl alcohol (t-BuOH)
   - 3) Chlorine (Cl₂), Dichloromethane (CH₂Cl₂)

**Structures of Possible Products:**

1. **First Structure:**
   - Benzene ring attached to a 3-chloropropene with the double bond in trans configuration. 
   - Hydrogen atom at the first carbon of the propene chain.

2. **Second Structure:**
   - Benzene ring attached to a 3,3-dichloropropene.
   - Both chlorine atoms attached at the same carbon.

3. **Third Structure:**
   - Benzene ring attached to a saturated propyl chain with one chlorine substituent on each of the first two carbons.
   - The chlorine on the first carbon is on the opposite side (wedge) to the hydrogen on the second carbon (dash).

4. **Fourth Structure:**
   - Similar to the third structure, but both hydrogen atoms are on one side (wedge) and chlorine atoms on the opposite side (dash).

**Explanation of Process:**

- **Step 1** involves deprotonation of the alkyne followed by nucleophilic substitution to form the propargylic intermediate.
- **Step 2** likely involves anti addition, transforming the alkyne to a trans-alkene or adjusting the stereochemistry.
- **Step 3** introduces chlorine atoms. The process indicates a preference for anti-addition, where chlorines add across the double bond.

**Diagrams Interpretation:**

These structures illustrate possible outcomes based on the orientation (cis/trans) and stereochemistry (enantiomers) of chlorine addition. Understanding these will help predict the most stable configuration leading to the major product shown.
Transcribed Image Text:**Title: Reaction Sequence and Stereochemistry** **Question:** What is the major final product of the following reaction sequence? Only one enantiomer of the possible products is shown. **Reaction Sequence:** 1. Starting material: Benzyl bromide 2. Reagents and conditions: - 1) Sodium hydride (NaH), Tetrahydrofuran (THF) - 2) Sodium, Ammonia (liquid), tert-Butyl alcohol (t-BuOH) - 3) Chlorine (Cl₂), Dichloromethane (CH₂Cl₂) **Structures of Possible Products:** 1. **First Structure:** - Benzene ring attached to a 3-chloropropene with the double bond in trans configuration. - Hydrogen atom at the first carbon of the propene chain. 2. **Second Structure:** - Benzene ring attached to a 3,3-dichloropropene. - Both chlorine atoms attached at the same carbon. 3. **Third Structure:** - Benzene ring attached to a saturated propyl chain with one chlorine substituent on each of the first two carbons. - The chlorine on the first carbon is on the opposite side (wedge) to the hydrogen on the second carbon (dash). 4. **Fourth Structure:** - Similar to the third structure, but both hydrogen atoms are on one side (wedge) and chlorine atoms on the opposite side (dash). **Explanation of Process:** - **Step 1** involves deprotonation of the alkyne followed by nucleophilic substitution to form the propargylic intermediate. - **Step 2** likely involves anti addition, transforming the alkyne to a trans-alkene or adjusting the stereochemistry. - **Step 3** introduces chlorine atoms. The process indicates a preference for anti-addition, where chlorines add across the double bond. **Diagrams Interpretation:** These structures illustrate possible outcomes based on the orientation (cis/trans) and stereochemistry (enantiomers) of chlorine addition. Understanding these will help predict the most stable configuration leading to the major product shown.
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