ch 23/24/25/26 reagents

Br, FeBr3 OR any halogen

Adds halogen to benzene

Cl-X, AlCl3

Friedel-Crafts Alkylation

Substitutes hydrogen for alkyl (X) group

Only with sp3 hybridized carbon on X group

O=CX, AlCl3

Friedel Crafts Acylation

HCl, Zn(Hg)

Removes carbonyl entirely

HNO3 (concentrated), H2SO4

Adds nitro group (NO2) to benzene

H2SO4 (concentrated) - ONLY

Adds SO3H group to benzene

CAN BE REMOVED BY PLACING IT IN WATER

KMnO4, X-OH; Acid workup (H3O+)

Changes any alkyl group on benzene into a COOH

Cleaves off any group that has carbon directly attached to benzene

• EXCEPT for quaternary carbon (sp3)

H2, Pd

Reduces nitrobenzene into aromatic amine

-NO2 group → NH2 group

HCl, Fe

Reduces nitrobenzene into aromatic amine

-NO2 group → NH2 group

NaNO2, H2SO4

Sandmeyer Reaction

Makes -NH2 group into -N=N group

CuBr/CuCN/CuCL

Sandmeyer Reaction

Replaces -N=N group with atom attached to Cu (Br, Cl, or CN)

KI

Replaces -N=N group with -I

HBF3

Replaces -N=N group with F

H2O, Cu2O, Cu(NO3)2

Replaces -N=N group with -OH

H3PO4

Replaces -N=N group with H (removes group entirely)

ortho/para directors

Has electrons attached to atom on benzene that can be donated to resonance

-Cl, -NH2, -OH, CH3 (oddly)

USUALLY activating (except for halogens)

meta directors

Does NOT have electrons attached to the atom on benzene; cannot be donated to resonance

-NO2,

ALWAYS deactivating

PBr3/ PCl3/ SOCl2

Replaces -OH with halogen

PCl3 with another halogen gas (Br2)

Places halogen gas atom (Br) at alpha spot next to carbonyl

adding a ___ makes an activating group deactivating, therefore preventing overreactions or meta substituents instead of ortho/para

acid (H2SO4, CH3CO2H)

LiOH

Reduces amides/esters

OsO4, H2O2, alcohol solvent

Adds -OH to both carbons of an alkene in the SAME direction stereochemically

KMnO4, KOH (acid workup)

Adds -OH to both carbons of an alkene in the SAME direction stereochemically

To alkynes, add -OH to both carbons and then make them ketones to rid the leftover alkene between the two C

HIO4, THF

Splits molecule in the middle of alcohols

Will keto-enol tautomerize (make ketones/aldehydes)

O3, H3CSCH3 (or Zn, HoAC)

Splits molecule in the middle of alcohols

Will keto-enol tautomerize (make ketones/aldehydes)