1) I am asked to provide the starting material with formula C4H9BrO that reacts with a bulky base (KOC(CH3)3) to generate cyclobutanol (C4H8O). I was wondering how this mechanism would work as I thought a bulky base would necessarily favor an E2 reaction, and we would get an alkene, which is not the product of cyclobutanol generated.

2) If neomenthyl chloride is treated with NaOC2H5 in ethanol, mostly 3-methene is formed with some 2-menthene. I can see why 3-methene is formed, but I cannot explain/see how 2-methene might be formed.

3) If someone tries to form t-butyl ethyl ether from equimolar amounts of t-butyl bromide and sodium ethoxide, why isn't the desired product actually formed and what is formed instead? How might we form the desired product then? I thought sodium ethoxide was a strong nucleophile and would form the desired product.

4) If a compound A with formula C7H15Br that is not a primary alkyl bromide forms a single alkene B when heated with sodium ethoxide in ethanol, and then hydrogenation of B leads to 2,4-dimethylpentane, what might compounds A and B be? I am confused because I don't see how the B alkene can reasonably generate the 2,4-dimethylpentane.

5) I am asked to provide the starting material with formula C7H14O (a hint is that the IR shows strong absorbance at 3300 and weaker absorbance at 1657, leading me to think there is a O-H and C=O bond) that reacts with HgSO4 and NaBH4 (Markovnikov anti-addition oxy-mercuration demercuration mechanism) to form 1,1-dimethyl cyclopentanol (with formula C7H14O) with O as part of the ring. I am confused how the final product does not have an OH from the attack of water to open the mercurinium ion and subsequent deprotonation.