Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 13, Problem 2LGP
Interpretation Introduction

Interpretation:

The conversion of 2methyl2butene into 2methyl1,3butadiene and ethylbenzene into 3phenylacrylonitrile and the product of the Diels Alder reaction is to be determined.

Concept introduction:

▸ The reagent NBS is used for the allylic bromination of the alkene and the mechanism of the reaction involves the formation of free radicals.

▸ The dehydrohalogenation of halo alkene takes place in the presence of a base like KOH to form the alkene as a product.

▸ The process in which the alkene is treated with ammonia and oxygen for the formation of nitrile is known as Ammoxidation.

▸ A reaction in which dienes and dienophiles react with each other to form the cyclic compound is known as Diels Alder reaction.

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(a) Cyclohexa-1,3-diene can be converted into a tetrasubstituted haloalkane when reacted with bromine in ether. Write a balanced chemical equation for the reaction that occurs and state the expected observation.  (b) Compound A and B are alkenes with the same molecular formula C5H10. Compound A is a branched-chain alkene while compound B is a straight-chain alkene. The reaction between compound A with hydrogen bromide produces major product C which is optically active.  (i) Draw TWO (2) possible structures for compound B. (ii) Outline the mechanism for the reaction between compound A with hydrogen bromide to form major product C.  (iii) Name the product formed when compound A undergoes bromination reaction.
Explain why (i) the dipole moment in chlorobenzene is lower than that of cyclohexyl chloride. (ii) haloalkanes are only slightly soluble in water but dissolve easily in organic solvents.
Draw structural formulas for the following compounds:  (a) (2Z,4Z)-2,4-dibromo-3-methylhepta-2,4-diene (b) ((2E,4Z)-2-bromo-3,5-dichloro-4-methylhexa-2,4-diene

Chapter 13 Solutions

Organic Chemistry

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