I am attempting to study for a final and cannot figure out these practice synthesis problems in spite of my best efforts, does anyone have ideas...all begin with a benzene ring and all require multiple steps.
1) product = benzene ring with sec-butanol attached to it
- however the benzene ring has the double bonds in the resonance structure on the original
- I was thinking just do friedel-crafts alkylation, but then there is no rearrangement in the ring...
2) product = benzene with NO2 in the 1 position 3 position and 5 position, also there is a CH3 in the 4 position
- if i add CH3 again using friedel-crafts, can i do then do nitration w/ 3 eq.? HNO3/H2SO4, this would put everything in the correct ortho/para/meta positions, but I've never seen that done w/ 3 eq. and it doesn't seem right
Last one, starting w/ a 1-methylcyclohexene the product is 2-ethylnonan-2,7-ol (okay I'm bad with nomenclature so there are 9 carbons, and on the 2nd carbon there is an ethyl and an OH, and on the 7th carbon there is an OH). THis has something to do with Oxidation but if I oxidize with O3/ HOOH I still have the double bonds and no extra carbons.
Another totally unrelated question regarding thermodynamics and kinetics in 1,2 and 1,4 reactions like HBr or Br2. We are told we cannot go simply by temperature (made that mistake on the last test) to determine the product. However, is it that the more substitated product will form in greater quantities at higher temperatures, and the least substituated will form in greater quantities at lower temperatures regardless of the 1,2 and 1,4 positions? From there one can figure out the kinetic or thermodynamic control?
Sorry for the vast amount of questions, any help would be appreciated...