General reactions

add Br to alkane

Br2, hv

Add Br to next to a pi bond

NBS, hv

allylic bromination (pi intant, add to adjacent carbon

halogenation

alkene > HX

+H202 for antimark

acid catalyzed OH

alkene > H30+

rearrangement mark

Mercuration OH

alkene > 1) Hg(OAc)2, H20. 2) NaBH4

no rearrangemnt mark

Hydroboration OH

Alkene > 1)BH3 THF 2)H202, Naoh

Alkene to alkane

H2 Pt

Add Br across alkene

alkene >Br2

make halohydrin

alkene >Br2, H20

Trans dihydroxylation/diol

alkene 1)RCO3H 2)H30+

Syn dihydroxilation

Alkene > KMnO4 Naoh cold

1)OsO4

2)NaHSO3, H2o

Open ring up

alkene in ring > 1) O3 2)DMS

makes chain with ketone and aldehyde

Add carbon to alkyne

1)NaNH2 2)alkyl-X

Make alkyne

Geminal/vicinial dihalide > 1)XS NaNH2. 2)H20

Alkyne > ketone +Ch3

HgSO4, H2SO4, H20

Alkyne > aldehyde

1)R2BH

2)H2o2, NaoH

Alkyne > Carboxylic

1)O3 2)H20

terminal alkyne makes co2

Alkyne to alkene

H2 Lindlars (cis

LiNH3(l) trans

Make geminal dihalide

Alkyne >XS HX

Adds to same carbon

Make vicinal dihalide

X2 (1 equiv

CCl4