[Cooper]

Hi,

I do a lot of syntheses on paper for my orgo class and I come across this predicament a lot.

If I am adding HBr to an alcohol that also has an alkene, which one will the HBr react with? Will it react with both in varying amounts so that you get mixed products? I am assuming this is only a question when the carbon that the alcohol is on is tertiary, because it is an Sn1 reaction.

Thanks!

Also, on a non-chem note, is there anywhere on the website where you can view all the threads you are subscribed too?

[Hunter2]

The double bond is easier to react.  But it depends also on the side groups.

[Arkcon]

Also, on a non-chem note, is there anywhere on the website where you can view all the threads you are subscribed too?

You mean like this:  http://www.chemicalforums.com/index.php?action=profile;area=showposts;u=141795  Just click the username.

[Cooper]

@Hunter, thanks Do you know why it's easier to react?

@Arkcon, THANK YOU!!

[souro10]

I think acid-base reactions are the fastest to occur. Donating the lone pair on oxygen is both faster and energetically more favored, than breaking the double bond. Note that in either case there shall be a tertiary cation intermediate.