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Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein
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Identify the reagents necessary to achieve each

Chapter 10, Problem 10.6

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QUESTION:

Identify the reagents necessary to achieve each transformation below. In each case, you will need to use at least one reaction from this chapter and at least one reaction from the previous chapter. The essence of each problem is to choose reagents that will achieve the desired stereochemical outcome: Br (a) Br Br Br + En (b) OH OH + En (c) OH (d) OH OH OH + En (e) OH (f) OH

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QUESTION:

Identify the reagents necessary to achieve each transformation below. In each case, you will need to use at least one reaction from this chapter and at least one reaction from the previous chapter. The essence of each problem is to choose reagents that will achieve the desired stereochemical outcome: Br (a) Br Br Br + En (b) OH OH + En (c) OH (d) OH OH OH + En (e) OH (f) OH

ANSWER:

Step 1 of 15

(a)  This product is an anti addition of  \(\mathrm{Br}_{2}\), presumably across an alkene. The two methyl groups are also anti in the product, so they should be trans in the alkene used.

First, reduce the alkyne to a trans-alkene using Na in \(\mathrm{NH}_{3}\).

                                               

     

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