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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 106f(xi,xii)
Chapter 12, Problem 106f(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.'
(f) Chemical structure of a phenol with a hydroxyl group (OH) attached to a benzene ring.

Verified step by step guidance
1
Identify the structure of the given molecule: The molecule is a tertiary alcohol, specifically 2-phenyl-2-propanol.
Consider the reaction with HOCl, H₂O: Tertiary alcohols can undergo halogenation with HOCl to form alkyl chlorides. The hydroxyl group will be replaced by a chlorine atom.
Write the reaction mechanism for HOCl: The hydroxyl group is protonated by H⁺ from HOCl, forming water as a leaving group. The carbocation intermediate is then attacked by Cl⁻, resulting in the formation of 2-chloro-2-phenylpropane.
Consider the reaction with HIO₄: Periodic acid (HIO₄) is typically used to cleave vicinal diols (1,2-diols) into aldehydes or ketones. Since the given molecule is not a diol, no reaction will occur with HIO₄.
Summarize the products: The reaction with HOCl will yield 2-chloro-2-phenylpropane, while 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 Aromatic Substitution

Electrophilic aromatic substitution is a reaction where an electrophile replaces a hydrogen atom on an aromatic ring. In the context of phenols, the hydroxyl group (OH) activates the benzene ring, making it more susceptible to electrophilic attack, particularly at the ortho and para positions. This concept is crucial for predicting reactions involving aromatic compounds with substituents.
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Oxidation of Alcohols

Alcohols can undergo oxidation to form carbonyl compounds. The presence of oxidizing agents like HOCl can convert secondary alcohols into ketones. In the given structure, the tertiary alcohol group is resistant to oxidation under typical conditions, which is important for predicting the reaction outcome with oxidizing agents.
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Periodic Acid (HIO₄) Cleavage

Periodic acid (HIO₄) is known for cleaving vicinal diols, breaking the C-C bond between them to form carbonyl compounds. However, in the absence of vicinal diols, as in the given structure, no reaction occurs. Understanding this selective cleavage is essential for predicting the reactivity of compounds with periodic acid.
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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: (i) SOCl₂ ; (ii) PBr₃. If no reaction occurs, write 'no reaction.'

(k)

702
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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: (xi) HOCl, H2O (xii) HIO4 If no reaction occurs, write 'no reaction.'


(k)

715
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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.'


(k)

726
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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.'


(f)

805
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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.'

(f)

823
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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.'

(f)

736
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