Given that terminal alkynes react with bromine and water to yield bromoketones. A mechanism for the reaction is to be proposed. To what reaction of alkenes this reaction is analogous is also to be stated. Concept introduction: Addition of bromine to alkynes occurs through the formation of a cyclic bromonium ion intermediate. Water being nucleophilic, if present will attack the bromonium ion to yield an enol. The enol will then tautomerize to a ketone . Thus in thr product a bromine and a hydroxyl group are added to the triple bond. This reaction is similar to the addition of halohydrins to alkenes. To propose: A mechanism for the reaction in which ethynylbenzene reacts with bromine and water to yield a bromoketone is to be proposed. Further to state to what reaction of alkenes this reaction resembles.

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1. Predict the organic product(s) of the following reactions. Assume excess of reagents unless otherwise noted. a) &l BH3 •THF b) 1) NaOH 2) H3O+ solve d) ala 1) EtMgBr 2) H3O+ e) H2N سكر CuLi NH2 1) SOCI2 2) EtMgBr 3) H3O+ NC H3O+ Δ

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Question

Chapter 9.SE, Problem 29AP

Interpretation Introduction

Interpretation:

Given that terminal alkynes react with bromine and water to yield bromoketones. A mechanism for the reaction is to be proposed. To what reaction of alkenes this reaction is analogous is also to be stated.

Concept introduction:

Addition of bromine to alkynes occurs through the formation of a cyclic bromonium ion intermediate. Water being nucleophilic, if present will attack the bromonium ion to yield an enol. The enol will then tautomerize to a ketone. Thus in thr product a bromine and a hydroxyl group are added to the triple bond. This reaction is similar to the addition of halohydrins to alkenes.

To propose:

A mechanism for the reaction in which ethynylbenzene reacts with bromine and water to yield a bromoketone is to be proposed. Further to state to what reaction of alkenes this reaction resembles.

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