4. The 'H NMR spectrum of the product is provided. a) Use the spectrum to determine the product of the reaction. b) Propose a mechanism for the reaction. c) Is the reaction SN1, SN2, E1, or E2? а) NaCI SN1 or SN2? Br 2.0 1.5 1.0 0.5 0.0 integration: 6 2 2 8 (ppm) теchanism: b) он E1 or E2? H3O* singlet triplet singlet triplet quartet doublet triplet 7 6 4 3 2 1 integration: 2 2 1 1 8 (ppm) mechanism:

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**Transcription and Explanation**

**Problem 4:**

The provided text and diagrams relate to nuclear magnetic resonance (NMR) spectroscopy, a powerful analytical technique used in determining the structure of organic compounds. Below are detailed descriptions and analyses of the NMR spectra for two different chemical reactions.

**a) Reaction Analysis:**

- **Starting Material:** A compound with a bromine atom attached to a carbon chain is reacting with sodium chloride (NaCl).
- **¹H NMR Spectrum:** The spectrum shows peaks that correspond to different hydrogen environments within the molecule.
  - **Integrations:** 6, 2, 2
  - **Chemical Shifts (δ ppm):** Peaks around 1.5, 1.0, and 0.8 ppm.
  
**Proposed Mechanism:**
- The reaction is likely a nucleophilic substitution involving the displacement of bromine by a chloride ion. The reaction type should be identified as either Sₙ1 or Sₙ2.

**b) Reaction Analysis:**

- **Starting Material:** A phenylpropanol compound reacts with hydronium ions (H₃O⁺).
- **¹H NMR Spectrum:** Peaks are visible, corresponding to different hydrogen environments:
  - **Integrations:** 2, 2, 1, 1
  - **Splitting Patterns:** Doublet, triplet, singlet, quartet
  - **Chemical Shifts (δ ppm):** Notably, there are aromatic peaks around 7 ppm and aliphatic peaks between 1.0 and 3.0 ppm.

**Proposed Mechanism:**
- The reaction may involve an elimination process to form an alkene, requiring the determination if it is an E1 or E2 mechanism.

**Graphical Explanation:**
Each spectrum displays chemical shifts on the x-axis measured in parts per million (ppm), which indicate the relative environment of protons in the compounds. The number of signals and their splitting patterns can help deduce the structure of the product by matching known splitting rules for different proton types (e.g., singlet, doublet, triplet).

Students are encouraged to analyze the provided spectra and apply their understanding of NMR, reaction mechanisms, and organic chemistry principles to solve the given problem by determining the reaction pathways and types.
Transcribed Image Text:**Transcription and Explanation** **Problem 4:** The provided text and diagrams relate to nuclear magnetic resonance (NMR) spectroscopy, a powerful analytical technique used in determining the structure of organic compounds. Below are detailed descriptions and analyses of the NMR spectra for two different chemical reactions. **a) Reaction Analysis:** - **Starting Material:** A compound with a bromine atom attached to a carbon chain is reacting with sodium chloride (NaCl). - **¹H NMR Spectrum:** The spectrum shows peaks that correspond to different hydrogen environments within the molecule. - **Integrations:** 6, 2, 2 - **Chemical Shifts (δ ppm):** Peaks around 1.5, 1.0, and 0.8 ppm. **Proposed Mechanism:** - The reaction is likely a nucleophilic substitution involving the displacement of bromine by a chloride ion. The reaction type should be identified as either Sₙ1 or Sₙ2. **b) Reaction Analysis:** - **Starting Material:** A phenylpropanol compound reacts with hydronium ions (H₃O⁺). - **¹H NMR Spectrum:** Peaks are visible, corresponding to different hydrogen environments: - **Integrations:** 2, 2, 1, 1 - **Splitting Patterns:** Doublet, triplet, singlet, quartet - **Chemical Shifts (δ ppm):** Notably, there are aromatic peaks around 7 ppm and aliphatic peaks between 1.0 and 3.0 ppm. **Proposed Mechanism:** - The reaction may involve an elimination process to form an alkene, requiring the determination if it is an E1 or E2 mechanism. **Graphical Explanation:** Each spectrum displays chemical shifts on the x-axis measured in parts per million (ppm), which indicate the relative environment of protons in the compounds. The number of signals and their splitting patterns can help deduce the structure of the product by matching known splitting rules for different proton types (e.g., singlet, doublet, triplet). Students are encouraged to analyze the provided spectra and apply their understanding of NMR, reaction mechanisms, and organic chemistry principles to solve the given problem by determining the reaction pathways and types.
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