Organic Reactions...?

Question

Can someone help me with this.., having trouble getting the right answers of products for

"3-methyl-3-pentanol reacts with HBr at room temperature"

"2-ethyl-1-butanol reacts with thionyl chloride in the presence of pyridine (SOCl2)"

Answer 1

Product 1: 3-methyl-2-pentene, HBr, and Water.
Reaction 1 is alkene formation by dehydration.

Product 2: 1-Chloro-2-ethylbutane and junk.
Recation 2 is substition of OH with Cl. I think this is an SN1 reaction but I'm not sure. I'm sure about the product though.

Answer 2

After a few years of memorizing all the organic chemistry without actually understanding it, I took ionic organic chemistry which was a graduate level course. It basically allowed you to look at any set of chemicals and figure out what was likely to react. It was actually easier than memorizing all the reaction. I don't know if that is helpful besides saying there is a light at the end of the tunnel. You can tell from the relative proclivity (searching for a word) of a particular groups to give up electrons. It does have to do with the electronegativies but it is more about how free the electron pairs are able to move from atom to atom. You need to have groups or atoms that can take electrons when there are electrons to give. You have to think about it from the point of view of certain groups attracting electrons that might make it easier for another group to form a bond there. It was quite a while ago when I took the course. I only knew it as ionic organic chemistry. It would be worth looking into because you seem to have anticipated it.

Answer 3

draw the structure and then apply the 'rules' when reacting with HBr and thionyl chloride in SOCl2

Answer 4

draw out the reagents and starting materials and start looking for possible reactions. remember what makes a good nucleophile or electrophile, and it will get easier