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

Solution for problem 41SP Chapter 6

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 41SP

Show how you would convert (in one or two steps) 1-phenylpropane to the three products shown below. In each case, explain what unwanted reactions might produce undesirable impurities in the product.

Step-by-Step Solution:
Step 1 of 3

Solution 41SP

  1. - Bromosuccinimide (NBS) also works for brominating benzylic positions, next to aromatic ring. The 1-phenylpropane reacts with NBS for form 1-bromo-1-phenylpropane.

    For efficient bromination, a large concentration of bromine using must be avoided because can also be added to the double to form dibromo compound (undesired product)

(b)

The 1-phenylpropane reacts with NBS to form 1-bromo-1 phenylpropane. The 1-bromo-1-phenylpropane reacts with ethoxide ion by 2 mechanism to form 1-methoxy-1-phenylpropane. Here, the 1-bromo-1-phenylpropane is a secondary alkyl halide. This is also favorable for 1 mechanism. In 1 mechanism, the undesired products are also formed.

(c)

The 1-phenylpropane reacts with NBS to form 1-bromo-1-phenylpropane. The 1-bromo-1-phenylpropane reacts with sodium ethoxide in ethanol by E2 mechanism to form 1-phenylprop-1-ene. Here, the methanol is polar protic solvent. In the presence of polar protic solvents, the 1 reacts is proceeds to form undesirable products.

Step 2 of 3

Chapter 6, Problem 41SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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