Ochem addition rxns

Question 1

Solvents used for demercuration

Answer 1

NaBH4
NaOH, H2O (base and water)

Question 2

Pick faster rxn
Terminal 2 vs internal 2

Internsl 2 vs internal 3

Answer 2

Terminal 2
Internal 3

Question 3

What breaks up boraine and what is that solvents structure

Answer 3

THF solvent

Pentane w/ O (in middle)

Question 4

solvent: HX (x=halide)

Answer 4

hydrogenation
alkene attack H, carbocation on more sub of double, halide attcks carbocation to form new bond

Question 5

solvent: acid, h2o, h3o

Answer 5

acid catalyzed hydration
alkene attack H, carbocation on more sub of double, whole water attacks carbocation to create new bond and another water added to deprotonate water

Question 6

solvent: 1) Hg(AOC)2 2)NaBH4

Answer 6

oxymercuration/demercuration

OH forms at more subs part of double bond while HgOAC forms at less subs side. use NaBH4 to get rid of mercury

Question 7

solvent: THF BH3

Answer 7

hydroboration oxiadation
forming of H and OH where OH at less sub. same face. dont forget if there’s methyl to add wedge/dash (if chiral)

Question 8

solvent: H2, pt

Answer 8

catalytic hydrogenation
removal of alkene- dont forget if there’s methyl to add wedge/dash (if chiral). same face (syn)

Question 9

solvent:X2 (halide, except I2)

Answer 9

halogenation
addition of x2 ACROSS alkene (anti) dont forget if there’s methyl to add wedge/dash (if chiral).

Question 10

solvent: 1) I2, Br2 2)ch2cl3, ch3oh, h20

Answer 10

halohydrin
instead of both x2 getting in, we get OH at more sub and one of the X-X. anti addition. dont forget if there’s methyl to add wedge/dash (if chiral).

Question 11

anti vs syn dihydroxylation
-solvents, and what is added

Answer 11

anti: 1) Rco3H 2) H3O
syn: Kmno4, NaOH, OsO4

both are adding 2 oh (across/same face- depending on solv). dont forget if there’s methyl to add wedge/dash (if chiral).

Question 12

what solvents creates OH

Answer 12

THF BH3 (oh at less sub)
mercury Hg(AOC)2 (at more subs)

H3O,H20,OR H2SO2 (whol h20 and then depro- at more subs)

h2o with x2
instead of both x, it is h20 and gets depro (oh at more sub)

anti/syn addition (for 2 oh)

Question 13

naoet, DBU partnered w/

Answer 13

DMSO (aprotic)