Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination

Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition

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Mullins 1st Edition

Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination

Problem 106f(i-xii)

Chapter 12, Problem 106f(i-xii)

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)

Verified step by step guidance

Identify the functional groups present in molecule (f) to determine how it might react with each reagent.

For reaction (i) with SOCl₂, consider if there is an alcohol group present, as SOCl₂ is commonly used to convert alcohols to alkyl chlorides.

For reaction (ii) with PBr₃, check for the presence of an alcohol group, since PBr₃ is used to convert alcohols to alkyl bromides.

For reaction (iii) with SOCl₂ and NEt₃, recognize that NEt₃ is a base that can facilitate the conversion of alcohols to alkyl chlorides by neutralizing the HCl byproduct.

For reaction (iv) with TsCl and Et₃N followed by NaCN, understand that TsCl converts alcohols to tosylates, which are good leaving groups, allowing NaCN to perform a nucleophilic substitution to form a nitrile.

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Key Concepts

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

Reagents and Their Functions

Understanding the specific reagents mentioned in the question, such as SOCl₂, PBr₃, and TsCl, is crucial. Each reagent has distinct roles in organic reactions, such as converting alcohols to alkyl halides or facilitating nucleophilic substitutions. Familiarity with these reagents helps predict the products formed during the reactions.

Mechanisms of Organic Reactions

Organic reactions often follow specific mechanisms, such as SN1, SN2, E1, or E2 pathways. Recognizing the mechanism allows for predicting the outcome of reactions based on the structure of the reactants and the conditions provided. This understanding is essential for determining whether a reaction will proceed and what products will be formed.

Functional Group Transformations

Functional groups are specific groups of atoms within molecules that determine their chemical reactivity. The question involves various transformations, such as oxidation and substitution, which change the functional groups present in the molecules. A solid grasp of how different reagents affect functional groups is necessary to accurately predict the products of the reactions.

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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: (xi) HOCl, H₂O (xii) HIO₄ 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:(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: (vii) HCl; (viii) HBr; 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: (xi) HOCl, H₂O (xii) HIO₄ If no reaction occurs, write 'no reaction.'

(f)

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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)

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