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Ch. 9 - Substitution and Elimination Reactions of Alkyl Halides
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Non è quello che usi tu?Cambia libro di testo
Capitolo 9, Problema 99a,b

What are the products of the following reactions?
a.
b.

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1
Step 1: Analyze the first reaction. The reactant is an alkyl iodide (1-iodobutane), and the reagent is triethylamine ((CH₃CH₂)₃N). This reaction involves nucleophilic substitution, where the iodide group is replaced by the nucleophile.
Step 2: In the first reaction, triethylamine acts as a nucleophile. It will attack the carbon bonded to iodine, displacing the iodide ion (I⁻) and forming a new bond between the carbon and the nitrogen of triethylamine.
Step 3: Analyze the second reaction. The reactant is a chiral alkyl chloride (2-chlorobutane), and the reagent is a thiolate ion (CH₃S⁻). This reaction also involves nucleophilic substitution, where the chloride group is replaced by the nucleophile.
Step 4: In the second reaction, the thiolate ion (CH₃S⁻) will attack the carbon bonded to chlorine, displacing the chloride ion (Cl⁻) and forming a new bond between the carbon and the sulfur of the thiolate group.
Step 5: Consider stereochemistry for the second reaction. Since the carbon bonded to chlorine is chiral, the nucleophilic substitution may proceed via an SN2 mechanism, leading to inversion of configuration at the chiral center.

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