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 106o(i-xii)

Chapter 12, Problem 106o(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.'
(o)

Verified step by step guidance

Identify the functional group in the given molecule. The structure shows a secondary alcohol attached to a benzene ring.

Consider the reaction with SOCl₂. This reagent typically converts alcohols into alkyl chlorides via an S_N2 mechanism, which may lead to inversion of configuration.

For the reaction with PBr₃, expect a similar transformation as with SOCl₂, converting the alcohol into an alkyl bromide, again with potential inversion of configuration.

When SOCl₂ is used with NEt₃, the reaction proceeds similarly to SOCl₂ alone, but NEt₃ acts as a base to neutralize the HCl byproduct, facilitating the formation of the alkyl chloride.

For the reaction sequence with TsCl and Et₃N followed by NaCN, the alcohol is first converted to a tosylate, which is a good leaving group, and then undergoes nucleophilic substitution with NaCN 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 reactants. A solid grasp of how different functional groups react under various conditions is vital for accurately predicting the products.

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Textbook Question

Triphenylphosphine and iodine can be used to convert alcohols to iodoalkanes. Suggest a mechanism for this reaction. [Triphenylphosphine first acts as a nucleophile in this reaction.]

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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.

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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.'

(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: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; 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: (vii) HCl; (viii) HBr; If no reaction occurs, write 'no reaction.'

(o)

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Textbook Question

Another method for converting alcohols to chloroalkanes makes use of chlorotrimethylsilane (TMSCl) and DMSO. Suggest a mechanism for this reaction to form (a) a 1° chloroalkane and (b) a 3° chloroalkane. [The reaction begins by the reaction of DMSO and TMSCl and is analogous to the Swern oxidation.]

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