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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 106o(xi,xii)
Chapter 12, Problem 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.

Verified step by step guidance
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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Key Concepts

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

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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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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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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Related Practice
Textbook Question

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'

(o)

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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: (ix) PCC; (x) H₂CrO₄ , H₂O. If no reaction occurs, write 'no reaction.'

(o)

1
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Textbook Question

Cleavage of the following ether produces the alcohol and haloalkane only, regardless of how much HBr is used. Thinking about the mechanism of the reaction, explain why bromobenzene is not also a product of this reaction.

1
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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 (iv) 1. TsCl, Et₃N 2. NaCN; If no reaction occurs, write 'no reaction.'

(o)

1
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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 ; (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ (vii) HCl; (viii) HBr; (ix) PCC; (x) H₂CrO₄ , H₂O (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'

(o)

1
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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.'

(o)

2
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