VIPSolutionsgive answer in 2 step with explanation at the end of each step and final answer at the end:7) Propose a synthesis of the following 5pts o oN oH - ww >
Question:
give answer in 2 step with explanation at the end of each step and final answer at the end:
7) Propose a synthesis of the following 5pts
o
oN
oH - ww >
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Asked by: Rahul
Created at: 2025-11-17 14:21:47
Asked by: Rahul
Created at: 2025-11-17 14:21:47
Final Answer:
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## Step 1: Convert Acrylic Acid to 1,3-Dibromopropane
**Reagent:** 1) Reduction (LiAlH4), 2) PBr3, 3) KCN
- First, reduce acrylic acid (propenic acid) to 1-propanol using LiAlH4.
- Then, convert 1-propanol to 1,3-dibromopropane by first converting it to 1,3-dibromopropane via bromination steps.
**Explanation:**
Reduction of the carboxylic acid gives 1-propanol. Bromination at both ends (via PBr3 and then NBS/Br2 with light for allylic bromination) can give 1,3-dibromopropane.
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## Step 2: Double Nitrile Substitution
**Reagent:** 2 eq. NaCN (sodium cyanide, SN2 reaction)
- React 1,3-dibromopropane with NaCN to substitute both bromine atoms with CN groups, yielding 1,3-propanedinitrile.
**Explanation:**
An SN2 reaction will replace both bromine atoms with cyanide ions, giving the required dinitrile.
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## **Final Answer:**
### **Synthesis Steps**
1. **Reduce acrylic acid to 1-propanol** (LiAlH4), then **convert to 1,3-dibromopropane** (PBr3/NBS/Br2).
2. **React 1,3-dibromopropane with NaCN** to get 1,3-propanedinitrile (NC-CH₂-CH₂-CN).
**Overall Reaction:**
Acrylic acid → (LiAlH4, then PBr3/NBS/Br2) → 1,3-dibromopropane → (2 NaCN) → 1,3-propanedinitrile
**Note:** If direct conversion to 1,3-dibromopropane is too complex, a possible alternative is:
Acrylic acid → 3-bromopropanoic acid (Br₂, hv) → 1,3-dibromopropane (PBr₃) → dinitrile (NaCN).
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