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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 106k(xi,xii)
Chapter 12, Problem 106k(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.'


(k) Chemical structure of a cyclohexanol derivative with an attached hydroxyl group.

Verified step by step guidance
1
Identify the functional groups present in the given molecule. The structure shows a cyclohexane ring with a tertiary alcohol group attached.
Consider the reaction conditions (xi) HOCl, H₂O. This is a hypochlorous acid in water, which typically adds across double bonds or reacts with alcohols to form chlorohydrins.
Since the molecule contains a tertiary alcohol, HOCl can react with the alcohol to form a chlorohydrin. The hydroxyl group will be replaced by a chlorine atom.
Next, consider the reaction conditions (xii) HIO₄. Periodic acid (HIO₄) is known for cleaving vicinal diols (1,2-diols) into aldehydes or ketones. However, since the molecule does not have a vicinal diol, no reaction will occur under these conditions.
Summarize the expected outcomes: Under condition (xi), the tertiary alcohol will be converted to a tertiary chloride. Under condition (xii), no reaction will occur as there is no vicinal diol present.

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Key Concepts

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

Oxidation of Alcohols

Oxidation of alcohols involves the conversion of an alcohol group into a carbonyl group. Primary alcohols can be oxidized to aldehydes or further to carboxylic acids, while secondary alcohols are typically oxidized to ketones. Tertiary alcohols generally do not undergo oxidation under mild conditions due to the lack of a hydrogen atom on the carbon bearing the hydroxyl group.
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Periodic Acid (HIO₄) Cleavage

Periodic acid (HIO₄) is used to cleave vicinal diols, breaking the C-C bond between the two hydroxyl-bearing carbons and forming two carbonyl compounds. This reaction is specific to 1,2-diols and does not occur if the hydroxyl groups are not adjacent. In the absence of vicinal diols, no reaction occurs with HIO₄.
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Reactivity of HOCl with Alcohols

Hypochlorous acid (HOCl) can react with alcohols to form alkyl hypochlorites, which can further undergo rearrangement or elimination reactions. The reaction is more favorable with primary and secondary alcohols, where the formation of a carbocation intermediate is possible. Tertiary alcohols may not react significantly due to steric hindrance and the stability of the starting material.
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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)

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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: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'

(k)

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

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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)

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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)

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.'


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