Unit 7 Test Reagents

benzene + X2/FeX2 —>

benzene + HNO3 / H2SO4 —>

benzene + SO3/H2SO4 —>

benzene + ROH / H2SO4

benzene with R group attached

(use an alcohol over an acid to oxidize)

benzene + RCl / AlCl3 —>

benzene with R group attached

**friedel-crafts alkylation

benzene + Cl-COR / AlCl3

bezene with COR attached

**friedel-crafts acylation

benzene with side chain + Br2 / hv OR NBS / hv

brominates the side chain at carbon attached to benzene

benzene with side chain + KMNO4 (STRONG OXIDIZER)

oxidizes WHOLE side chain to COOH

benzene with COR attached + Zn(Hg) / HCl or NH2NH2 / -OH

reduces to just CH2R

benzene with NO2 attached + Fe/HCl or Sn/HCl

benzene with NH2 attached

carbonyl + NaBH4 / CH3OH

alcohol (C=O) becomes C-OH

Carbonyl + 1. LiAlH4 / 2. H2O

alcohol (C=O) becomes C-OH

carbonyl + CrO3 / H3O+

NO REACTION

THIS IS JONES REAGENT

carbonyl + Ag2O / ethanol

NO REACTION

THIS IS TOLLENS REAGENT

carbonyl + 1. R—Li / 2. H2O or 1. R—MgBr / 2. H2O

C=O turns to C—OH and add an R group to the center carbon

carbonyl + NaCN / H—Cl

C=O becomes C—OH

add CN to center carbon (carbon now has 4 things)

carbonyl + RNH2 / mild acid such as CH3COOH

C=O becomes C=N—R

*(makes an imine)

carbonyl + R2NH / mild acid such as CH3COOH

C=O becomes NR2

make one of the C—C bonds next to C=O become a C=C bond

*(makes an enamine)

carbonyl + H2O / H+ or OH-

carbonyl becomes C(OH)2

carbonyl + CH3OH, H+ / (2 equiv.)

C=O becomes C(O-)2

R—X + PBr3

RBr

RBr + Mg / diethyl ether

R—MgBr

R—X + 2Li

RLi + LiX

Benzene + I2 / CuCl2

benzene with I added

benzene/nucleophile + alkene / h2SO4

Add the alkene to the benzene / nucleophile

MAKE SURE U HAVE RIGHT AMOUNT OF CARBONS