4. Propose a reasonable starting material for each of the following reactions: LDA 4. CN NACN. NAOH

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**Question 4: Propose a reasonable starting material for each of the following reactions:**

1. **Reaction with LDA**  
   - **Product:** Cyclohexene with a double bond.
   - **Explanation:** Propose an appropriate starting material that will convert to the given cyclohexene using the reagent LDA (Lithium Diisopropylamide).

2. **Reaction with NaCN**  
   - **Product:** Benzyl cyanide (phenylacetonitrile).
   - **Explanation:** Identify a starting compound that, upon reaction with NaCN, will yield benzyl cyanide.

3. **Reaction with NaOH**  
   - **Product:** 1-Phenyl-1-butene.
   - **Explanation:** Determine which precursor could react with NaOH to produce the alkene shown.

4. **Reaction with HBr**  
   - **Product:** Bromocyclohexane with a variable substitution.
   - **Explanation:** Indicate a suitable starting material that, in the presence of HBr, will form the depicted bromocyclohexane.
Transcribed Image Text:**Question 4: Propose a reasonable starting material for each of the following reactions:** 1. **Reaction with LDA** - **Product:** Cyclohexene with a double bond. - **Explanation:** Propose an appropriate starting material that will convert to the given cyclohexene using the reagent LDA (Lithium Diisopropylamide). 2. **Reaction with NaCN** - **Product:** Benzyl cyanide (phenylacetonitrile). - **Explanation:** Identify a starting compound that, upon reaction with NaCN, will yield benzyl cyanide. 3. **Reaction with NaOH** - **Product:** 1-Phenyl-1-butene. - **Explanation:** Determine which precursor could react with NaOH to produce the alkene shown. 4. **Reaction with HBr** - **Product:** Bromocyclohexane with a variable substitution. - **Explanation:** Indicate a suitable starting material that, in the presence of HBr, will form the depicted bromocyclohexane.
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LDA (Lithium diisopropyl amide) is a hindered base which can cause elimination reactions. Hoffman products (less substituted alkenes) are the major product. 

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