4. Use the NMR chemical shifts table provided in the lecture slides to answer the following questions. a. Briefly rationalize, based on chemical fundamentals and the physics of NMR chemical shift, why the aldehyde proton is at 9.5 ppm, the chloromethyl proton at-3.5 ppm, and a standard methyl proton at 1 ppm. A good answer should be -4-6 sentences. b. A compound "A" of chemical formula C3H6CI2 has the NMR spectrum below. What is its structure? Briefly explain your reasoning.

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### NMR Chemical Shifts and Structural Analysis

**Problem 4: Use the NMR chemical shifts table provided in the lecture slides to answer the following questions.**

**a.** Briefly rationalize, based on chemical fundamentals and the physics of NMR chemical shift, why the aldehyde proton is at ~9.5 ppm, the chloromethyl proton at ~3.5 ppm, and a standard methyl proton at ~1 ppm. A good answer should be 4-6 sentences.

**b.** A compound “A” of chemical formula C₃H₆Cl₂ has the NMR spectrum below. What is its structure? Briefly explain your reasoning.

**NMR Spectrum Description:**
- The spectrum shows two main peaks labeled:
  - **B** at 3.75 ppm
  - **A** at 2.20 ppm
- There are integration values indicating the relative number of hydrogens contributing to each signal.
- The TMS peak for reference is at 0 ppm.

**c.** Compound A can form polymers by reacting with H₂N-CH₂-CH₂-CH₂-CH₂-NH₂. What is the mechanism of the polymerization reaction?

**d.** Draw the mechanism for the formation of a monomer unit using the arrow formalism.

**e.** Will this reaction yield only linear polymers (like Nylon) or will it also yield branching? Briefly explain your answer. Draw arrows for reaction if necessary.
Transcribed Image Text:### NMR Chemical Shifts and Structural Analysis **Problem 4: Use the NMR chemical shifts table provided in the lecture slides to answer the following questions.** **a.** Briefly rationalize, based on chemical fundamentals and the physics of NMR chemical shift, why the aldehyde proton is at ~9.5 ppm, the chloromethyl proton at ~3.5 ppm, and a standard methyl proton at ~1 ppm. A good answer should be 4-6 sentences. **b.** A compound “A” of chemical formula C₃H₆Cl₂ has the NMR spectrum below. What is its structure? Briefly explain your reasoning. **NMR Spectrum Description:** - The spectrum shows two main peaks labeled: - **B** at 3.75 ppm - **A** at 2.20 ppm - There are integration values indicating the relative number of hydrogens contributing to each signal. - The TMS peak for reference is at 0 ppm. **c.** Compound A can form polymers by reacting with H₂N-CH₂-CH₂-CH₂-CH₂-NH₂. What is the mechanism of the polymerization reaction? **d.** Draw the mechanism for the formation of a monomer unit using the arrow formalism. **e.** Will this reaction yield only linear polymers (like Nylon) or will it also yield branching? Briefly explain your answer. Draw arrows for reaction if necessary.
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