Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
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Chapter 7, Problem 7.61P
Interpretation Introduction

Interpretation: A stepwise mechanism of the given reaction is to be drawn and an explanation corresponding to the statement that 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under SN1 reaction conditions, even though it is a 1° alkyl halide, is to be stated.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron rich chemical species that contains negative charge or lone pair of electrons are known as a nucleophile. In a nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking the electron deficient carbon atom.

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Determine a stepwise mechanism for the following reaction that illustrates why two substitution products are formed. Explain why 1-bromohex-2-ene reacts rapidly with a weak nucleophile (CH3OH) under Syl reaction conditions, even though it is a 1° alkyl halide. 1-bromohex-2-ene Part 1: Br CH₂OH The first step in the reaction proceeds according to which mechanism? CH₂CH₂CH₂CH=CHCH₂ + CH₂OH CH₂CH₂CH₂CH: Part 2: Br CHCH₂ Draw the missing resonance contributor. OCH3 + CH3CH₂CH₂CH=CHCH₂ CH3CH₂CH₂CH=CH-CH₂ + Br Br OCH 3 H₂CH₂CH₂CH=CH₂ view structure + + Br HBr X
Provide reagents and reaction conditions for each step
1. Which alkene is the major product of this dehydration? HO H2SO4 heat А В C D
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