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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblem 106a(xi,xii)
Chapter 12, Problem 106a(xi,xii)

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (xi) HOCl, H₂O (xii) HIO₄. If no reaction occurs, write 'no reaction.'  
(a) Chemical structure of phenol, featuring a hydroxyl group (OH) attached to a benzene ring.

Verified step by step guidance
1
Identify the functional group in the given molecule. The structure shown is benzyl alcohol, which contains a primary alcohol group attached to a benzene ring.
Consider the reaction with HOCl, H₂O. HOCl is a source of hypochlorous acid, which can oxidize primary alcohols to aldehydes or carboxylic acids under certain conditions.
Predict the product of the reaction with HOCl, H₂O. In this case, the primary alcohol group in benzyl alcohol is likely to be oxidized to a carboxylic acid, resulting in benzoic acid.
Consider the reaction with HIO₄. Periodic acid (HIO₄) is typically used to cleave vicinal diols (1,2-diols) into aldehydes or ketones. Since benzyl alcohol does not contain a vicinal diol, no reaction is expected with HIO₄.
Summarize the expected outcomes: The reaction with HOCl, H₂O will likely yield benzoic acid, while the reaction with HIO₄ will result in 'no reaction' as there is no vicinal diol present in the molecule.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a reaction in which an electrophile replaces a hydrogen atom on an aromatic ring. In the context of phenol, the hydroxyl group activates the benzene ring towards electrophilic attack, making it more reactive. The presence of HOCl can lead to chlorination of the aromatic ring, typically at the ortho or para position relative to the hydroxyl group.
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Oxidative Cleavage with Periodic Acid (HIO₄)

HIO₄ is a reagent used for oxidative cleavage of vicinal diols, breaking the C-C bond between them to form carbonyl compounds. However, in the case of phenol, there are no vicinal diols present, so HIO₄ would not react with the structure. Therefore, no reaction is expected when phenol is treated with HIO₄.
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Phenol Reactivity

Phenol is an aromatic compound with a hydroxyl group directly attached to the benzene ring, which significantly influences its reactivity. The hydroxyl group donates electron density into the ring, enhancing its reactivity towards electrophiles. This makes phenol more susceptible to reactions like halogenation, where electrophiles such as HOCl can add to the ring, typically at the ortho and para positions.
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Related Practice
Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O. If no reaction occurs, write 'no reaction.'  

(a)

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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iv) 1. TsCl, Et₃N 2. NaCN ; (v) 1. TsCl, Et₃N 2. NaOt-Bu . If no reaction occurs, write 'no reaction.'  

(a)

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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (i) SOCl₂ ; (ii) PBr₃. If no reaction occurs, write 'no reaction.'  

(a)

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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vii) HCl; (viii) HBr. If no reaction occurs, write 'no reaction.'  

(a)

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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (vii) HCl; (viii) HBr; If no reaction occurs, write 'no reaction.'

(c)

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Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iii) SOCl2 , NEt3. If no reaction occurs, write 'no reaction.'  

(a)

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