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Ch. 24 - Benzene 2: Reactions Influenced by the Aromatic Ring
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
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Tutti i libri di testoMullins 1st EditionCh. 24 - Benzene 2: Reactions Influenced by the Aromatic RingProblema 35c
Capitolo 23, Problema 35c

Suggest the reagents used to effect the transformations shown.
(c) Chemical reaction showing ether cleavage, producing a phenol and a cyclic ether. Reagents for transformation suggested.

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1
Identify the starting material and the products. The starting material is an ether with a phenyl group and a cyclopropyl group. The products are toluene and cyclopropanol.
Recognize that the transformation involves breaking the ether bond and forming an alcohol group on the cyclopropyl moiety while converting the phenyl group to toluene.
Consider the mechanism of ether cleavage. Acidic conditions are typically used to cleave ethers, often involving a strong acid like HBr or HI.
Propose the use of a strong acid such as HBr or HI to cleave the ether bond. The acid will protonate the ether oxygen, making it a better leaving group.
The protonated ether can then undergo nucleophilic attack by the halide ion, leading to the formation of toluene and cyclopropanol as the final products.

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Ether Cleavage

Ether cleavage involves breaking the C-O bond in ethers, typically using strong acids like HI or HBr. The reaction often results in the formation of alcohols and alkyl halides. In this transformation, the ether is cleaved to produce a phenol and a cyclic ether, indicating the use of acidic conditions to facilitate the cleavage.
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Percorso guidato
1:45
Cleavage of Phenyl Ethers Concept 1

Acidic Conditions

Acidic conditions are crucial for ether cleavage, as they protonate the ether oxygen, making the C-O bond more susceptible to nucleophilic attack. Common acids used include hydrobromic acid (HBr) or hydroiodic acid (HI), which can effectively cleave ethers to form alcohols and other products, as seen in the transformation to phenol and a cyclic ether.
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Using factors affecting acidity to rank acids

Phenol Formation

Phenol formation in ether cleavage reactions occurs when the aromatic ring stabilizes the resulting carbocation, allowing the formation of a stable phenol product. This stability is due to resonance within the aromatic ring, which is a key factor in the transformation shown, where the ether is cleaved to yield a phenol and a cyclic ether.
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Identify the most acidic phenol
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In the second propagation step in the bromination of toluene, Br2 is only attacked by a radical on the substituent carbon. Why?

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Suggest the reagents used to effect the transformations shown.

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(b) Why is only partial racemization sometimes observed?


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Oxidation of the phenol shown gives a single quinone product. Predict this product and explain why it is the only one formed.

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