Selecting Reagents to Accomplish Functional Group Transformation

9 Selecting Reagents to Accomplish Functional Group Transformation 

PRACTICE the skill 7.31 Determine whether each of the following reactions proceeds via an S l or Sfj2 mechanism and then draw the product(s) of the reaction  

32 In Chapter 23, we will learn several methods for making primary amines (RNH2). Each of these methods utilizes a different approach for forming the C—N bond. One of these methods, called the Gabriel synthesis, forms the C—N bond by treating potassium phthalimide with an alkyl halide  

The first step of this process occurs via an S 2 mechanism. Using this information, determine whether the Gabriel synthesis can be used to prepare the following amine. Explain your answer. 

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More than fifteen years have elapsed since this method was developed, but it has not lost any utility in natural product synthesis. It remains one of the most utilized haloalkene preparation methods. Even in cases where a substrate possesses a lot of sensitive functional groups and chiral centers, selective transformation to the ( )-haloalkene can be accomplished with this reagent. 

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