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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(v,vi)
Chapter 12, Problem 106f(v,vi)

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

Verified step by step guidance
1
Identify the starting material: The given molecule is a tertiary alcohol, specifically 2-methyl-2-phenylpropan-2-ol.
Step (v) involves two reactions: First, treat the alcohol with TsCl (tosyl chloride) in the presence of Et₃N (triethylamine). This converts the alcohol into a tosylate, a good leaving group.
Next, treat the tosylate with NaOt-Bu (sodium tert-butoxide). This is a strong base, which will likely lead to an elimination reaction, forming an alkene through an E2 mechanism.
Step (vi) involves treating the product with H₂SO₄ (sulfuric acid). In the presence of a strong acid, the alkene may undergo further reactions such as hydration or polymerization, depending on the conditions.
Consider the stability of potential products: The most stable alkene is typically the major product in elimination reactions, following Zaitsev's rule, which favors the formation of the more substituted alkene.

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Key Concepts

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

Reactivity of Alcohols

Alcohols can undergo various reactions depending on their structure and the reagents used. In the presence of TsCl (tosyl chloride) and a base like Et₃N (triethylamine), alcohols can be converted into better leaving groups, facilitating nucleophilic substitution or elimination reactions. Understanding the reactivity of alcohols is crucial for predicting the products of the reactions described.
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Nucleophilic Substitution and Elimination Reactions

Nucleophilic substitution (SN1 and SN2) and elimination (E1 and E2) are fundamental reaction mechanisms in organic chemistry. The choice of reagents, such as NaOt-Bu (sodium tert-butoxide), influences whether a substitution or elimination pathway is favored. Recognizing the conditions that favor each mechanism is essential for predicting the outcome of the reactions in the question.
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Acid-Catalyzed Reactions

Acid-catalyzed reactions, such as those involving H₂SO₄ (sulfuric acid), often lead to the formation of carbocations, which can rearrange or react with nucleophiles. This concept is vital for understanding how alcohols can be dehydrated to form alkenes or undergo other transformations. Knowing how acids interact with organic molecules helps in predicting the products of the reactions specified.
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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 ; (iii) SOCl₂, NEt₃. 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: (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: (iii) SOCl₂ , NEt₃ (iv) 1. TsCl, Et₃N 2. NaCN; 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: (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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