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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(iii,iv)
Chapter 12, Problem 106f(iii,iv)

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) Chemical structure of a phenol with a hydroxyl group (OH) attached to a benzene ring.

Verified step by step guidance
1
Identify the functional group in the given molecule. The structure shows a tertiary alcohol group attached to a benzene ring.
Consider the reaction conditions (iii) SOCl₂, NEt₃. This is a common method for converting alcohols to alkyl chlorides via the formation of a chlorosulfite intermediate.
In the presence of SOCl₂ and NEt₃, the hydroxyl group (OH) of the tertiary alcohol will be replaced by a chlorine atom, resulting in the formation of a tertiary alkyl chloride.
Now consider the reaction conditions (iv) 1. TsCl, Et₃N 2. NaCN. The first step involves converting the alcohol to a tosylate, which is a good leaving group, using TsCl and Et₃N.
In the second step, the tosylate reacts with NaCN, leading to a nucleophilic substitution where the tosylate group is replaced by a cyano group (CN), forming a nitrile.

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Key Concepts

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

Thionyl Chloride (SOCl₂) Reactivity

Thionyl chloride is a reagent commonly used for converting alcohols into alkyl chlorides. It reacts with alcohols to form the corresponding alkyl chloride and byproducts of sulfur dioxide and hydrochloric acid. Understanding this reaction mechanism is crucial for predicting the products when alcohols are treated with SOCl₂ in the presence of a base like NEt₃, which helps to neutralize the generated HCl.
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Synthesis of Acid Chlorides

TsCl and Base Reaction

TsCl, or tosyl chloride, is used to convert alcohols into tosylates, which are better leaving groups for subsequent nucleophilic substitutions. When combined with a base like Et₃N, the tosylate can then react with nucleophiles such as NaCN in a second step. This two-step process is essential for understanding how to predict the final products of the reaction sequence involving TsCl and NaCN.
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Recognizing Acid-Base Reactions.

Nucleophilic Substitution Mechanisms

Nucleophilic substitution reactions, such as SN1 and SN2, are fundamental in organic chemistry for understanding how nucleophiles attack electrophiles. The choice of mechanism depends on factors like substrate structure and the nature of the nucleophile. Recognizing whether a reaction will proceed via SN1 or SN2 is vital for predicting the outcome of reactions involving alkyl halides and nucleophiles like NaCN.
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Nucleophiles and Electrophiles can react in Substitution Reactions.
Related Practice
Textbook Question

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


(c)

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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.'

(c)

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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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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.'

(f)

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