Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 25, Problem 26P
Interpretation Introduction

Interpretation:

A mechanism for the given reaction has to be proposed; and the formation of the products is to be explained.

Concept introduction:

The electrophilic addition reaction refers to the reaction in which first an electrophile attacks the substrate molecule across the C=C bond and results in the formation of carbocation.

The carbocation further reacts with electron rich molecule to form a covalent bond in the final product. In such reactions, the breaking of π bond results in the formation of two σ bonds.

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Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamylgroups. Disiamylborane is prepared by the reaction of BH3 # THF with an alkene.(a) Draw the structural formulas of the reagents and the products in the preparation ofdisiamylborane.(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why isSia3B not formed?
(a) What reagents would be used for the conversion of alkene A into the target? (b) What reaction is involved in the conversion of alcohol B into alkene A? Suggest a reagent that might affect this transformation. (c) Give a retrosynthetic analysis showing the disconnection of B, the synthons produced that lead to the synthetic equivalents given (draw their structures).
(c) Arrange the following compounds in order of increasing acidity, and explain the reasons fo your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluoronhenol
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