Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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
Transcribed Image Text:### Chemical Reaction Pathway and Product Identification
#### Reactants and Conditions:
- **Starting Material**: Benzaldehyde (C₇H₆O)
- Structure: A benzene ring bonded to an aldehyde group.
- **Reagents and Conditions**:
1. **Potassium cyanide (KCN) in water (H₂O)**
2. **Sodium borohydride (NaBH₄) in methanol (MeOH)**
3. **Cyclopentanone, p-Toluenesulfonic acid (TsOH), benzene, heat**
#### Possible Products:
The goal is to determine the major product of the multi-step reaction sequence.
**Possible Products (Labeled A-D):**
- **Product A**:
- Contains a benzyloxy group and cyclopentyl ring connected via an aromatic system.
- Structure: Benzene ring – O – (cyclopentyl group) - single bond - Benzene ring.
- **Product B**:
- Features a benzyl and a phenyl group connected to a cyclopentane ring via an oxygen atom.
- Structure: Includes both benzyl and phenyl groups with stereochemistry indicated.
- **Product C**:
- Similar to B but with a different configuration and aromatic substituent.
- Structure: Benzyl group and cyclopentyl ring connected to a carbon with oxygen atoms.
- **Product D**:
- A benzyl group attached to a carboxylic acid functional group and phenyl group.
- Structure: Carboxylic acid derivative with a benzyl phenyl attachment.
## Explanation:
1. **Step 1** - **Potassium Cyanide (KCN) in Water**:
- Reacts with benzaldehyde to form a cyanohydrin via nucleophilic addition reaction.
2. **Step 2** - **Sodium Borohydride (NaBH₄) in Methanol**:
- Reduces the cyanohydrin intermediate to produce an amino alcohol compound.
3. **Step 3** - **Cyclopentanone, TsOH in Benzene Under Heat**:
- The resulting amino alcohol undergoes an acid-catalyzed intramolecular cyclization with cyclopentanone, leading to the formation of a bicyclic compound.
Given the conditions
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