Product Predictions

orgo midterm reactions to know the products and reactions

phenol

OH, ortho/para

toluene

CH3, ortho attack

aniline

lone pair NH2, ortho/para

anisole

OCH3, ortho

acetophenone

C=O-CH3, meta

benzaldehyde

C=O-H, meta

benzoic acid

C=O-OH, meta

chlorination

Add Cl to benzene

iodination

add I to benzene

Nitro reduction Zn/HCl, Sn/ HCl, Fe/ HCl,

NO2—> NH2

Sulfonation

SO3, H2SO4, hso4- (conjugate base)

Desulfonation H2SO4, heat

remove SO3H

Clemmensen Zn Hg, HCl

C=O—> all O’s turn into H’s

oxidation KMNO4, OH-, heat

any benzylic (meaning anything with a carbon next to the ring can turn into) COOH

Benzylic Halogenation Br2, NBS, hv

replace Benzyllic H (the hydrogen next to C it wont work with terbutyl atoms) with Br

Benzylic SN1

replace LG via carbocation

Benzylic SN2

1 step mechanism strong NUC, replace LG via backside attack

Phenol EAS

directs ortho para

NH2

ortho/para

hydride shift when

2—> 3 more stable carbocation, meaning more substituted!

OR aka OCH3

Ortho/ para

alkyl groyps (CH3, CH2CH3)

ortho/para

Halogens (Cl, Br, I…)

Direct ortho para, but are weak deactivators

Halogens are deactivators since they react slower than benzene. ‡

Halogens are ortho, para-directors because the halogen can stabilize the sigma complex.

electronegative and can withdraw electron density from the ring along the sigma bond.

NO2

meta deactivator

COOH

meta, deactivator, partial +C, with - O creates difference in electronegativity as a system

CHO

meta, deactivator

COR

meta, deactivator

COOR

meta, deactivator

CN

meta, deactivator

Deactivators and properties

Most electron-withdrawing groups are deactivators and meta-directors. ‡

The atom attached to the aromatic ring has a positive or partial positive charge. ‡ Electron density is withdrawn inductively along the sigma bond, so the ring has less electron density than benzene, and thus it will be slower to react