EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393630817
Author: KARTY
Publisher: W.W.NORTON+CO. (CC)
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Chapter 12, Problem 12.63P
Interpretation Introduction

(a)

Interpretation:

A method for conversion of hex-1-yne to 2, 2-dibromohexane is to be proposed.

Concept introduction:

The carbon-carbon triple bond of an alkyne undergoes electrophilic addition when treated with a strong Bronsted acid. In the first step, the proton is added to a carbon-carbon triple bond to form a vinylic cation. The conjugate base of the acid then coordinates with the cation. An alkene is formed which adds another molecule of the acid as it has one more π bond. The result is a geminal di-substituted product. When alkynes are treated with an excess of a hydrogen halide, a geminal dihalide is formed.

Interpretation Introduction

(b)

Interpretation:

A method for conversion of hex-1-yne to 1, 2-dibromohexane is to be proposed.

Concept introduction:

The oxidation of terminal alkyne is carried out by using bulky dialkylborane like disiamylborane [(C5H11)2BH] instead of simple borane (BH3) to avoid the formation of a mixture of products. After the first addition, no further addition takes place as the reagent does not have another B-H bond. Oxidation of the adduct by the action of NaOH and H2O2 initially forms an enol form which tautomerizes to the more stable keto form.

Sodium borohydride, NaBH4, reduces aldehydes to corresponding primary alcohols. Alcohol is dehydrated on heating with a strong acid like H2SO4 forming the corresponding alkene.

The electrophilic addition of molecular bromine across the double bond of an alkene forms a vicinal dibromide. The addition of molecular bromine involves a cyclic bromonium intermediate, either above or below the plane of the double bond, leading to the formation of a racemic mixture of the products.

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Chapter 12 Solutions

EBK ORGANIC CHEMISTRY: PRINCIPLES AND M

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