addition reaction

[koolman]

We have to find the compound C .

Why the product I formed is wrong and how is the correct product is formed .

Edited May 23, 2016 by Samagra

[Sensei]

What instantly appeared in my mind, watching your pictures, is that you didn't draw Hydrogen atoms.

You have Bromine connected to Carbon, which is connected to other Carbon. But you should have BrCH₂CH..

This lead to further errors.

 

IMHO, you should draw this in the first place:

Edited May 23, 2016 by Sensei

[hypervalent_iodine]

Sensei is correct to say that you should be drawing in your hydrogen atoms. When you are writing in the C's, the hydrogen a must also be included. I personally prefer using the zig zag style of drawing molecules, but not all students are immediately comfortable with this.

 

He also eluded to, but didn't explicitly mention the fact that your starting material is chemically incorrect and makes little sense. CO2Me is a methyl ester group. You did not draw a methyl ester group.

 

Some other points before we get to your main problem. Your title indicates that you think this is an addition reaction. It is not. It is a substitution reaction. Secondly, in your first mechanistic step, you drew the Ag+ ion attacking the double bond. Ignoring the fact that this wouldn't happen, it doesn't make chemical sense to have an electrophile attacking a nucleophile. By convention, we always write the nucleophile (the thing with the electrons) attacking the electrophile (the thing without).

 

Now then. Your main issue is that AgF is not a reagent for the addition of F across a double bond, and you're just not going to have silver bonding to a carbon like that. I mentioned what sort of reaction this is above, but consider the other reactive points in your molecule and what the AgF provides a source of. It may also be useful to consider the types of salts that Ag prefers to make (consider the hard / soft nature).