Question

The Gabriel synthesis transforms an alkyl halide into a primary amine via a two-step process. Follow the directions below to draw the initial mechanism and final products. Draw curved arrows to the next step. Draw the missing nonbonding electrons, charge and curved arrows. The first three steps are correct. I am unsure about how to complete the final step. Any help is much appreciated!

Draw curved arrows to the next step. Draw the missing nonbonding electrons, charge and curved arrows Draw the final products with nonbonding electrons. Complete the intermediate by drawing the missing atoms, bonds and nonbonding electrons.

Answer 1

Concepts and reason

Gabriel synthesis: Gabriel synthesis is a synthesis of the primary amine from the primary alkyl halide, in the presence of potassium phthalimide. Potassium phthalimide attacks the carbon atom of the alkyl halide and replaces the halide ion.

Fundamentals

Gabriel synthesis pathway: The primary amine synthesis from the primary alcohol is shown below.

It is clear from the above path that the phthalimide acts as a nucleophile and attacks the primary alkyl halide in the S_N2 path way, where chlorine is the leaving group.

The given alkyl halide is drawn below and the expected Gabriel synthesis product is also drawn below.

The curved arrow mechanism of the reaction is drawn below.

The products are drawn below for the final step of the synthesis.

The curved arrow mechanism for the final step is drawn below.

The major product during the Gabriel synthesis process is drawn below.

Ans:

The major product during the Gabriel synthesis process is drawn below.