Orgo Synthesis Reactions

O3, DMS

Does oxidative cleavage, splits at a double bond

OsO4, NMO

Adds 2 OH groups, syn

Pd/C, H2 (Alkene)

Syn addition of 2 H

m-CPBA

Creates two bonds to an oxygen (triangle), syn

H2O, H3O+

Adds 2 OH groups, anti

X2, H2O

Adds an X group and an OH group, markov, anti

X2

Adds 2 X groups, anti

Hg(OAc)2, H2O, NaBH4

Adds OH group, markov

BH3, H2O2, NaOH

Adds OH group, anti-markov, syn

TsCl, pyridine

Creates OTs group from OH group

HBr, ROOR

Adds Br group, anti-markov

HX

Adds X group, markov

EtONa/EtO-

Zaitsev elimination

tert-butyl ONa/Tert-butyl O-

Hofmann elimination

NaNH2 (xs), H2O

Turns vicinal/geminal dihalides into terminal alkyne

9-BBN, H2O2, NaOH

Turns terminal alkyne into aldehyde

HgSO4, H2O, H2SO4

Turns terminal alkyne into ketone

NaNH2, RX

Turns terminal alkyne into internal alkyne

Pd/C, H2 (alkyne)

Turns internal alkyne into alkane

Lindlar’s Cat, H2

Turns internal alkyne into syn alkene

Na, NH3

Turns internal alkyne into anti alkene

Br2, hv

Turns alkane into alkyl bromide, markov

NBS, hv

turns allylic/benzylic alkane into alkyl bromide, markov

ROOR, hv

Turns alkene into repeating polymer

Metal hydride (NaH, KH)

Turns alcohol into alkoxide

NaBH4

Reduces aldehydes and ketones

LiAlH4

Reduces aldehydes, ketones, esters, and carboxylic acids

R-MgX

Turns carbonyl into OH and adds R group to the C O is on