Question

Which of the following hydrocarbons is expected to be the most reactive in ethanloic silver nitrate? Why? Write the organic product that you expect when your chosen substrate reacts.

[URL=http://s1185.photobucket.com/user/terrazygote/media/Question%201.jpg.html][IMG]http://i1185.photobucket.com/albums/z354/terrazygote/Question%201.jpg[/IMG][/URL]

Draw the conjugate acid of compound A. Explain you choice.

[URL=http://s1185.photobucket.com/user/terrazygote/media/Question%202.jpg.html][IMG]http://i1185.photobucket.com/albums/z354/terrazygote/Question%202.jpg[/IMG][/URL]

Provide a mechanism. Include all intermediates. Show all electron pushing.

[URL=http://s1185.photobucket.com/user/terrazygote/media/Question%203.jpg.html][IMG]http://i1185.photobucket.com/albums/z354/terrazygote/Question%203.jpg[/IMG][/URL]

Answer 1

The given links are unable to open ... But you can go to the fact , that If the given compound has been shown to contain a halogen ( it may alkyl , vinyl or aryl) , the alkyl halides are reactive toawards the ehanolic siver nitrate , because the halogen is easily substituted by a neucleophile . the vinyl and aryl halides are unreactive as substitution of halogen does not occur easily.

considering the reaction occurs as:      

        R-X + OH^- ------------> R-OH + X^-

       Ag⁺_(aq) +   X^-_(aq) --------------> AgX

overall reaction :

R-x + CH3CH2OH ------_^AgNO3------> R-OCH2CH3 + AgX_ppt. + H⁺ + NO₃^-

The reaction of an alkyl halide with ehanol in presence of silver nitrate proceeds through SN1 mecahnism . The silver coordinates with the leaving group and helps form a carbocation . The ethanol solvent will act as a neucleophile , forming an ethyl ether.

As the mechanism of SN1 reactions are concerned , it proceeds via 2 steps 1) fromation of carbocation intermediate (slow process) 2) C-Nu bond formation (fast)

For a generalisation you can see :

I think this will somewhat related to your answer.