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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 106a(iv,v)
Chapter 12, Problem 106a(iv,v)

Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (iv) 1. TsCl, Et₃N 2. NaCN ; (v) 1. TsCl, Et₃N 2. NaOt-Bu . If no reaction occurs, write 'no reaction.'  
(a) Chemical structure of phenol, featuring a hydroxyl group (OH) attached to a benzene ring.

Verified step by step guidance
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Identify the starting material: The given structure is benzyl alcohol, which is a primary alcohol with the formula C₆H₅CH₂OH.
Step (iv) involves two reactions: First, treat the alcohol with TsCl (tosyl chloride) and Et₃N (triethylamine). This converts the alcohol into a tosylate, a good leaving group, forming C₆H₅CH₂OTs.
Next, react the tosylate with NaCN. The cyanide ion (CN⁻) acts as a nucleophile and performs an SN2 substitution, replacing the tosylate group with a cyano group, resulting in benzyl cyanide (C₆H₅CH₂CN).
Step (v) also begins with the conversion of the alcohol to a tosylate using TsCl and Et₃N, forming C₆H₅CH₂OTs.
React the tosylate with NaOt-Bu (sodium tert-butoxide). The tert-butoxide ion is a strong base and can cause elimination (E2 reaction), leading to the formation of styrene (C₆H₅CH=CH₂) by removing a hydrogen and the tosylate group.

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Key Concepts

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

TsCl and Et₃N Reaction

TsCl (tosyl chloride) is a reagent used to convert alcohols into better leaving groups by forming tosylates. When combined with Et₃N (triethylamine), a base, it facilitates the substitution of the hydroxyl group, making the molecule more reactive towards nucleophiles in subsequent reactions.
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Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. The nature of the nucleophile, such as NaCN (sodium cyanide) or NaOt-Bu (sodium tert-butoxide), influences the reaction pathway, either favoring SN2 or E2 mechanisms depending on sterics and the substrate.
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Reactivity of Alkyl Halides

The reactivity of alkyl halides is determined by the structure of the halide and the nature of the leaving group. Primary alkyl halides typically undergo SN2 reactions, while tertiary halides favor E2 elimination. Understanding the substrate's structure is crucial for predicting the outcome of reactions involving nucleophiles and bases.
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Related Practice
Textbook Question

The reaction of alkoxides with haloalkanes is not a viable way to form ethers. (a) Why? (b) Why can thioethers be formed by an analogous 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.'  

(a)

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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.'  

(a)

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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. If no reaction occurs, write 'no reaction.'  

(a)

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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.'  

(a)

Textbook Question

Suggest a synthesis for the following molecules beginning with organic molecules containing three or fewer carbons. [You will need to use a protecting group in these syntheses.]

(c)

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