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Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
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Tutti i libri di testoMullins 1st EditionCh. 13 - Alcohols, Ethers and Related Compounds: Substitution and EliminationProblema 106o(xi,xii)
Capitolo 12, Problema 106o(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.'
(o) Chemical structure of a phenol with a hydroxyl group attached to a carbon chain.

Guida verificata passo dopo passo
1
Identify the functional groups present in the molecule. The given molecule is a secondary alcohol attached to a benzene ring.
Consider the reaction conditions (xi) HOCl, H₂O. This is a hypochlorous acid in water, which can oxidize alcohols to chlorohydrins.
Predict the product for reaction (xi). The secondary alcohol will react with HOCl to form a chlorohydrin, where the hydroxyl group is replaced by a chlorine atom.
Consider the reaction conditions (xii) HIO₄. Periodic acid (HIO₄) is known to cleave vicinal diols (1,2-diols) into aldehydes or ketones.
Predict the product for reaction (xii). Since the molecule does not contain a vicinal diol, no reaction will occur with HIO₄.

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Electrophilic Addition of HOCl

In the presence of HOCl and water, an electrophilic addition reaction can occur where the hydroxyl group (OH) and chlorine (Cl) add across a double bond. This reaction typically involves the formation of a chlorohydrin, where the OH group attaches to the more substituted carbon, and Cl attaches to the less substituted carbon, following Markovnikov's rule.
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1,2 vs 1,4 Addition

Oxidative Cleavage with Periodic Acid (HIO₄)

HIO₄ is used to cleave vicinal diols (1,2-diols) into aldehydes or ketones. The reaction involves the formation of a cyclic periodate intermediate, which breaks down to yield carbonyl compounds. This reaction is specific to diols that are adjacent, and if no such diol is present, no reaction occurs.
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Monosaccharides - Oxidative Cleavage

Structure and Reactivity of Phenols

Phenols are aromatic compounds with a hydroxyl group directly attached to the benzene ring. The presence of the hydroxyl group increases the electron density of the ring, making it more reactive towards electrophilic substitution. However, the specific structure in the image shows a secondary alcohol attached to a phenyl group, which may not directly undergo reactions typical for phenols.
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Identify the most acidic phenol
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