H A 1. KCN, H2O 2. NaBH4, MeOH 3. cyclopentanone TSOH, benzene heat Ph Ph o look & of OH D B Ph

Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
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Chapter16: Synthesis Workshop 1
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### 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
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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