Orgo 2 Exam 2 Reagents

Cl2, FeCl3 or AlCl3

adds Cl (halogenation)

Br2, FeBr3

adds Br (halogenation)

I2, HNO3

adds I (halogenation)

HNO3, H2SO4

adds NO2 (nitration)

SO3/H2SO4 or fuming H2SO4

add SO3H (sulfonation)

isopropyl chloride/ AlCl3

adds the hydrocarbon chain attached to atom (friedel crafts)

Hf/ 0 C orrrr BF3/ 60 C

add the hydrocarbon attached to the atom (friedel crafts)

acytl chloride with AlCl3/H20

adds ketone to the ring (friedel crafts)

SOCl2 or PCl5

carboxylic acid to acytl chloride

3 Cl2/hv

CH3 -> CCl3

Br2/hv

Adds Br onto methyl

NaOEt/EtOH with a primary leaving group

kicks off leaving group, adds oxygen with two carbons chain (ethyl) (SN2 reaction)

NaOEt/EtOH with a secondary leaving group

adds double bond in most stable potition

H+/heat

adds double bond in most stable position

HBr

adds Br in most stable position

HBr/ RO-OR

adds Br in less stable position

1. KMnO4, NaOH heat 2. H3O+

Methylbenzene to methyl carbolic acid (oxidation)

CH3Cl, AlCl3

add CH3 to benzene

CO, HCl/ AlCl3

adds aldehyde (gatterman- koch)

CH3COCl/ py

adds ketone to protect NH or OH or whatever

- allows for only para addition

NaOH/ heat

changes halogen to OH (SnAr)

NaNH2/NH3

changes leaving group to NH2

Na, CH3OH

takes away one double bond (Birch reduction)

1. NaNO2/HCl

2. H3O +

NH2 (analine) -> OH (phenol)

PCC/CH2Cl2

primary alcohol to aldehyde

secondary alcohols to ketone

DMSO (COCl)2, cold/Et3N

primary alcohol to aldehyde (swern)

secondary alcohol to ketone

O3, Me2S

break double bond and add a carbonyl to each side

LiLAH4

carboxylic acid to primary alcohol (reduction)

LiLAH (O tert-butyl)/H2O

acytl chloride -> primary alcohol carboxylic acid -> aldehyde

DIBAL-H, H2O

ester -> aldehyde

MgBr on a branched hydrocarbon/ H3O+

Nitrile to a Ketone

LiOH

carboxylic acid -> ketone

NH2-NH2/KOH heat

removes carbonyl off hydrocarbon chain (Wolff Kishner)