Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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What, if anything, would be different about the product of the reaction if you started with Z-stilbene instead of E-stilbene?

 

### Scheme 1: Overall Bromination Reaction
The first reaction starts with E-stilbene, which is converted into (1R,2S)-1,2-dibromo-1,2-diphenylethane using pyridinium tribromide in the presence of acetic acid at 50°C. The chemical reaction equation is:

- **Reactant:** E-stilbene
- **Reagent:** Pyridinium tribromide, Acetic acid, 50°C
- **Product:** (1R,2S)-1,2-dibromo-1,2-diphenylethane

### Scheme 2: Decomposition of Pyridinium Bromide
This scheme illustrates the decomposition process of pyridinium bromide upon heating. Pyridinium tribromide decomposes to produce pyridine, hydrogen bromide (HBr), and bromine (Br₂).

- **Reactant:** Pyridinium bromide
- **Products:** Pyridine, HBr, Br₂

### Scheme 3: Synthesis of Diphenylacetylene
The third scheme demonstrates the conversion of (1R,2S)-1,2-dibromo-1,2-diphenylethane into diphenylacetylene. This transformation uses potassium hydroxide (KOH) in ethanol under microwave conditions.

- **Reactant:** (1R,2S)-1,2-dibromo-1,2-diphenylethane
- **Reagents:** KOH (2 equivalents), EtOH, Microwave
- **Products:** Diphenylacetylene, H₂O, KBr

The reaction details depict a typical method of organic synthesis involving bromination and subsequent elimination to form an acetylene compound.
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Transcribed Image Text:### Scheme 1: Overall Bromination Reaction The first reaction starts with E-stilbene, which is converted into (1R,2S)-1,2-dibromo-1,2-diphenylethane using pyridinium tribromide in the presence of acetic acid at 50°C. The chemical reaction equation is: - **Reactant:** E-stilbene - **Reagent:** Pyridinium tribromide, Acetic acid, 50°C - **Product:** (1R,2S)-1,2-dibromo-1,2-diphenylethane ### Scheme 2: Decomposition of Pyridinium Bromide This scheme illustrates the decomposition process of pyridinium bromide upon heating. Pyridinium tribromide decomposes to produce pyridine, hydrogen bromide (HBr), and bromine (Br₂). - **Reactant:** Pyridinium bromide - **Products:** Pyridine, HBr, Br₂ ### Scheme 3: Synthesis of Diphenylacetylene The third scheme demonstrates the conversion of (1R,2S)-1,2-dibromo-1,2-diphenylethane into diphenylacetylene. This transformation uses potassium hydroxide (KOH) in ethanol under microwave conditions. - **Reactant:** (1R,2S)-1,2-dibromo-1,2-diphenylethane - **Reagents:** KOH (2 equivalents), EtOH, Microwave - **Products:** Diphenylacetylene, H₂O, KBr The reaction details depict a typical method of organic synthesis involving bromination and subsequent elimination to form an acetylene compound.
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