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Recall from Section 9-7 how acetylide ions are alkylated

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 21P Chapter 10

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 21P

Recall from Section 9-7 how acetylide ions are alkylated by displacing unhindered alkyl halides.

Like acetylide ions, Grignard and organolithium reagents are strong bases and strong nucleophiles. Fortunately, they do not displace halides as easily as acetylide ions do. If they did displace alkyl halides, it would be impossible to form the reagents from alkyl halides because whenever a molecule of reagent formed, it would react with a molecule of the halide starting material. All that would be formed is a coupling product. In fact, coupling is a side reaction that hurts the yield of many Grignard reactions.

Step-by-Step Solution:

Answer :

Step 1</p>

1-bromobutane reacts in the presence of lithium and copper iodide to and this on reacting with 1-bromo butane gives octane    

Step 2</p>

Ethylene bromide reacts in the presence of lithium and copper iodide to give intermediate and this on further reaction gives 3-phenylpropene.

Step 3 of 3

Chapter 10, Problem 21P is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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Recall from Section 9-7 how acetylide ions are alkylated

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