Organic Chemistry Predict Major Product

[NY152]

Homework Statement

Predict major product and what type of reaction mechanism

Homework Equations

The Attempt at a Solution

Top Problem: So the Bromine is a good leaving group, and is in the secondary position so you cannot rule out anything right away. The nucleophile is charged, so it will be either Sn2 or E2. I think it's E2 because the solvent is polar protic (O-).
So knowing the reaction mechanism is most likely E2 (I may be mistaken), I think the hydrogen (not shown) across from the bromine would be would be removed, and the electrons would then go in maybe? and create a double bond between the cyclopentane and the methyl substituent left...I'm just not sure how the two different solvents would affect this given one is in the primary position (maybe less stable so easier to leave?) and the other.Bottom Problem:

The hydroxyl group is in the secondary position, and going through similar logic like the top problem, I believe the reaction with HBr to be Sn1 (I think the HBr is neutral?), and the H2SO4 to be E1 due to the heat making it a dehydration mechanism. Similar to the top problem, my main difficulty is predicting the major product. I'm pretty sure for the E1 heat, a double bond will be created but I'm not sure how in a way that it will be stable.

 

[Asim Riaz]

My guesses are that the major product will be a cyclopentane with a double bond between the carbon and the methyl group for the top problem, and a cyclopentane with a double bond between the oxygen and the methyl group for the bottom problem.