For this assignment, the target compound that you should synthesize is benzyl methyl ether. This is...

For this assignment, the target compound that you should synthesize is benzyl methyl ether. This is a
substitution reaction. Examine the product and determine which bonds may be formed. Keep in mind the
substitution pattern of the product and the nature of the mechanism accommodated by this arrangement.

starting materials: benzyl chloride, ether, NaOMe

A. Approx TLC values of product and starting material

B. Write mechanism for this reaction

Solutions

Expert Solution

The reaction of benzyl chloride with strong base NaOMe is a nucleophilic substitution reaction which is a single step reaction. In this reaction there is a breaking of C-Cl bonds in benzyl chloride and formation of new C-O bond. It is an example of SN2 reaction, which is a second order reaction and the concentration of benzyl chloride and nucleophile (NaOMe) both affect the rate of reaction. Reaction proceeds through a transition state and this state includes the bond breaking (removal of leaving group Cl-) and bond forming (attack by nucleophile MeO-) steps togather in the molecule. The slowest step is the formation of transition state.

A. TLC analysis: in a given solvent (mobile phase) the Rf value for benzyl chlodide will be higher than product (benzyl methyl ether) because product benzyl methyl ether has a polar group OMe and this will make a strong interaction with stationary phase of TLC plate.
B. Reactiion mechanism:

queen_honey_blossom answered 1 year ago

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