Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 13, Problem 20P
Interpretation Introduction

Interpretation:

The products formed when 1,3-butadiene reacts with the given reagents are to be determined.

Concept introduction:

Hydrogenation with platinum as a catalyst is a reducing agent and can be used to convert unsaturated carbohydrates to saturated hydrocarbons.

Potassium permanganate oxidizes hydrocarbons to carbon dioxide. Also hot alkaline KMnO4 oxidatively cleaves alkenes to form carboxylic acids.

Alkenes react with halides and undergo substitution reaction where halides replace the double bonds. The product stereochemistry is dependent on the stereochemistry of the reactant alkene.

Conjugated dienes undergo both 1,2- and 1,4-electrophilic addition.

The 1,2 – addition to a diene is the addition of electrophile to the carbon designated as 1 and the nucleophile to the carbon designated as 2 as shown below. But the positions of carbons as 1 and 2 are not according to the IUPAC numbering of the molecule but as a conjugated diene. The mechanism is similar with 1,4-addition.

The mechanism of 1,2 addition and 1,4-addition of hydro halogenation is given below.

Organic Chemistry, Chapter 13, Problem 20P , additional homework tip  1

Organic Chemistry, Chapter 13, Problem 20P , additional homework tip  2

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Which compound does not exist? (a) 1,2,3,4,5,6,7-octaheptaene (b) cis-2-butane (c) trans-3-hexene (d) 1-propene (e) cis-4-decene
Draw a structural formula of an alkene that undergoes acid-catalyzed hydration to give each alcohol as the major product (more than one alkene may give each alcohol as the major product). (a) 3-Hexanol (b) 1-Methylcyclobutanol (c) 2-Methyl-2-butanol (d) 2-Propanol
Compounds B and C are hydrocarbons with the structural formulae as shown below. CH, „CH, в (a) Name compounds B and C according to the IUPAC nomenclature. (b) Both B and C can undergo oxidation reaction with the same oxidizing agent. Write chemical equations involved and explain the differences between these two reactions. (c) Name one reaction that converts B to methylcyclohexane.

Chapter 13 Solutions

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