Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.

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**Question 3:**

Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.

[Diagram of a molecular structure]

- The diagram shows a benzene ring attached to a carbon chain. The chain has a double bond at the second position. 
- An arrow indicates a specific hydrogen (proton) positioned on the single-bonded carbon adjacent to the benzene ring and double bond (allylic to both structures).

**Note:** Use the referenced tables to determine chemical shift values based on the molecular environment of the highlighted hydrogen.
Transcribed Image Text:**Question 3:** Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer. [Diagram of a molecular structure] - The diagram shows a benzene ring attached to a carbon chain. The chain has a double bond at the second position. - An arrow indicates a specific hydrogen (proton) positioned on the single-bonded carbon adjacent to the benzene ring and double bond (allylic to both structures). **Note:** Use the referenced tables to determine chemical shift values based on the molecular environment of the highlighted hydrogen.
**Table 22.3: Additive Parameters for Predicting NMR Chemical Shifts of Alkyl Protons in CDCl₃**

**Base Values:**
- Methyl: 0.9 ppm
- Methylene: 1.2 ppm
- Methine: 1.5 ppm

---

**Substitution Groups (Y) and Their Parameters:**

| Group (Y)            | Alpha (α) Substituent | Beta (β) Substituent | Gamma (γ) Substituent |
|----------------------|-----------------------|----------------------|-----------------------|
| —R                   | 0.0                   | 0.0                  | 0.0                   |
| —C≡C                 | 0.8                   | 0.2                  | 0.1                   |
| —C≡C—Arᵇ           | 0.9                   | 0.1                  | 0.1                   |
| —C≡C(C=O)OR         | 1.0                   | 0.3                  | 0.1                   |
| —C≡C—R              | 0.9                   | 0.3                  | 0.1                   |
| —C≡C—Ar             | 1.2                   | 0.3                  | 0.2                   |
| —Ar                  | 1.4                   | 0.4                  | 0.1                   |
| —C(=O)OH            | 1.1                   | 0.3                  | 0.1                   |
| —C(=O)OR            | 1.1                   | 0.3                  | 0.1                   |
| —C(=O)H             | 1.1                   | 0.4                  | 0.1                   |
| —C(=O)R             | 1.2                   | 0.3                  | 0.0                   |
| —C(=O)Ar            | 1.7                   | 0.3                  | 0.1                   |
| —C(=O)NH₂          | 1.0                   | 0.4                  | 0.1                   |
| —C(=O)Cl            | 1.8                   | 0.4
Transcribed Image Text:**Table 22.3: Additive Parameters for Predicting NMR Chemical Shifts of Alkyl Protons in CDCl₃** **Base Values:** - Methyl: 0.9 ppm - Methylene: 1.2 ppm - Methine: 1.5 ppm --- **Substitution Groups (Y) and Their Parameters:** | Group (Y) | Alpha (α) Substituent | Beta (β) Substituent | Gamma (γ) Substituent | |----------------------|-----------------------|----------------------|-----------------------| | —R | 0.0 | 0.0 | 0.0 | | —C≡C | 0.8 | 0.2 | 0.1 | | —C≡C—Arᵇ | 0.9 | 0.1 | 0.1 | | —C≡C(C=O)OR | 1.0 | 0.3 | 0.1 | | —C≡C—R | 0.9 | 0.3 | 0.1 | | —C≡C—Ar | 1.2 | 0.3 | 0.2 | | —Ar | 1.4 | 0.4 | 0.1 | | —C(=O)OH | 1.1 | 0.3 | 0.1 | | —C(=O)OR | 1.1 | 0.3 | 0.1 | | —C(=O)H | 1.1 | 0.4 | 0.1 | | —C(=O)R | 1.2 | 0.3 | 0.0 | | —C(=O)Ar | 1.7 | 0.3 | 0.1 | | —C(=O)NH₂ | 1.0 | 0.4 | 0.1 | | —C(=O)Cl | 1.8 | 0.4
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