IR spectrum of maleic anhydride 100 80 - 60 40 20 - 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 Wavenumber (cm-1) Transmittance (%)

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Given this Diels Alder experimental procedure. Make IR assignments for the given IR Spectrum.

**Experiment: Diels-Alder (D-A)**

**Title:** Diels-Alder Reaction (Otto and Kurt). Cycloaddition of Maleic Anhydride with Anthracene

**Reference:** Hill, R. K.; Barbaro, J. *Experiments in Organic Chemistry* (2000, 2nd Ed) pp E7-1-3.

**Purpose:** Synthesize 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride

---

### Reaction Scheme:

1. **Reactants:**
   - Anthracene
   - Maleic Anhydride

2. The reaction occurs with "reflux".

3. **Product:**
   - The resultant structure is 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride.

### Reagent Table:
| Reagent (Source)       | Mwt     | mp °C  | bp °C | (Fp)  | mmol | Mass (%) | Density | Volume |
|------------------------|---------|--------|-------|-------|------|----------|---------|--------|
| **anthracene** (Acros) | 178.23  | 216-8  | -     | (121) | 10.1 | 1.84 g (98%)  | -     | -      |
| **maleic anhydride** (Acros) | 98.06  | 54-56  | 200   | (103) | 10.1 | 1.00 g (99%)  | -     | -      |
| **toluene (anhyd.)** (Pharmaco) | -  | 111    | -     | -     | -    | -        | 0.87    | 43 mL  |
| **cycloadduct** | 276.29 | 261-2  | -     | -     | 10.1 | 2.79 g  | -     | -      |

**Date Revised:** 03/09/2010ssh

#### Diagram Explanation:
The schematic shows a Diels-Alder reaction between anthracene and maleic anhydride, indicating the reflux process used to form the cycloadduct. The structural formulae of the
Transcribed Image Text:**Experiment: Diels-Alder (D-A)** **Title:** Diels-Alder Reaction (Otto and Kurt). Cycloaddition of Maleic Anhydride with Anthracene **Reference:** Hill, R. K.; Barbaro, J. *Experiments in Organic Chemistry* (2000, 2nd Ed) pp E7-1-3. **Purpose:** Synthesize 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride --- ### Reaction Scheme: 1. **Reactants:** - Anthracene - Maleic Anhydride 2. The reaction occurs with "reflux". 3. **Product:** - The resultant structure is 9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic anhydride. ### Reagent Table: | Reagent (Source) | Mwt | mp °C | bp °C | (Fp) | mmol | Mass (%) | Density | Volume | |------------------------|---------|--------|-------|-------|------|----------|---------|--------| | **anthracene** (Acros) | 178.23 | 216-8 | - | (121) | 10.1 | 1.84 g (98%) | - | - | | **maleic anhydride** (Acros) | 98.06 | 54-56 | 200 | (103) | 10.1 | 1.00 g (99%) | - | - | | **toluene (anhyd.)** (Pharmaco) | - | 111 | - | - | - | - | 0.87 | 43 mL | | **cycloadduct** | 276.29 | 261-2 | - | - | 10.1 | 2.79 g | - | - | **Date Revised:** 03/09/2010ssh #### Diagram Explanation: The schematic shows a Diels-Alder reaction between anthracene and maleic anhydride, indicating the reflux process used to form the cycloadduct. The structural formulae of the
### IR Spectrum of Maleic Anhydride

**Description:**

The graph displayed represents the infrared (IR) spectrum of maleic anhydride. It provides a visual representation of transmittance (%) versus wavenumber (cm⁻¹).

**Axes:**

- **Y-Axis:** Transmittance (%) ranging from 0% to 100%.
- **X-Axis:** Wavenumber (cm⁻¹) spanning from 4000 cm⁻¹ to 600 cm⁻¹.

**Key Features:**

- The spectrum shows several distinct peaks at specific wavenumbers, indicating the presence of various functional groups within the molecule.
- A major absorption peak is notable around the 1800 cm⁻¹ region, characteristic of C=O stretching vibrations found in anhydrides.
- Other notable peaks appear below 1500 cm⁻¹, which may correspond to bending vibrations and other molecular interactions.

**Chemical Structure:**

Accompanying the spectrum is a structural diagram of maleic anhydride, emphasizing its cyclic anhydride form.

This type of IR spectrum is useful in identifying and confirming the presence of maleic anhydride in a sample by analyzing its specific vibrational modes and structural fingerprint.
Transcribed Image Text:### IR Spectrum of Maleic Anhydride **Description:** The graph displayed represents the infrared (IR) spectrum of maleic anhydride. It provides a visual representation of transmittance (%) versus wavenumber (cm⁻¹). **Axes:** - **Y-Axis:** Transmittance (%) ranging from 0% to 100%. - **X-Axis:** Wavenumber (cm⁻¹) spanning from 4000 cm⁻¹ to 600 cm⁻¹. **Key Features:** - The spectrum shows several distinct peaks at specific wavenumbers, indicating the presence of various functional groups within the molecule. - A major absorption peak is notable around the 1800 cm⁻¹ region, characteristic of C=O stretching vibrations found in anhydrides. - Other notable peaks appear below 1500 cm⁻¹, which may correspond to bending vibrations and other molecular interactions. **Chemical Structure:** Accompanying the spectrum is a structural diagram of maleic anhydride, emphasizing its cyclic anhydride form. This type of IR spectrum is useful in identifying and confirming the presence of maleic anhydride in a sample by analyzing its specific vibrational modes and structural fingerprint.
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