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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 106o(v,vi)
Chapter 12, Problem 106o(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.'
(o) Chemical structure of a phenol with a hydroxyl group attached to a carbon chain.

Verified step by step guidance
1
Identify the functional group in the given molecule. The structure shows a secondary alcohol attached to a benzene ring.
Consider the first set of reaction conditions: 1. TsCl, Et₃N. This step involves converting the alcohol into a tosylate, which is a good leaving group.
In the presence of TsCl (tosyl chloride) and Et₃N (triethylamine), the hydroxyl group (OH) is replaced by a tosylate group (OTs), making the molecule more reactive for the next step.
Consider the second step: NaOt-Bu. This is a strong, bulky base that typically promotes elimination reactions, leading to the formation of an alkene through an E2 mechanism.
For the second set of reaction conditions: H₂SO₄, this is a strong acid that can protonate the alcohol, leading to dehydration and formation of an alkene through an E1 mechanism. Analyze the structure to determine the most stable alkene product.

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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 these reactions.
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Nucleophilic Substitution Reactions

Nucleophilic substitution reactions involve the replacement of a leaving group by a nucleophile. The mechanism can be either SN1 or SN2, depending on the substrate and conditions. In this context, the use of NaOt-Bu (sodium tert-butoxide) suggests a strong base that can promote elimination or substitution, making it essential to determine the likely pathway and product.
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Acid-Catalyzed Reactions

Acid-catalyzed reactions, such as those involving H₂SO₄ (sulfuric acid), often facilitate the formation of carbocations or activate substrates for further reactions. In organic synthesis, acids can promote dehydration of alcohols or rearrangements, which can lead to different products. Recognizing the role of acids in these reactions is vital for predicting outcomes.
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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: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'

(k)

784
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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.'

(o)

782
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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.'


(k)

603
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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)

710
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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)

744
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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)

653
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