Organic Chemistry II Exam II Summer

Activator

alkyl, lone pair (except halogens)

Deactivator

partial positive, (+), halogens

Ortho/Para

alkyl, lone pair

Meta

partial positive, (+)

ortho, para directing/activating

NH2, OH, OR, NHCOCH3, -R (alkyl), -Benzene (aryl)

ortho, para directing/deactivating

halogens (F, Cl, Br, I)

meta directing/ deactivating

carbonyls, SO3H, CN, NO2, NR3li

limitations of friedel crafts

-reaction fails if benzene has a substitutent that is more deactivating than halogens

-reaction fails with unprotected NH2 and NR2.

what do you need to protect NH2?

acetic anhydride, (Ac2O/NaOAc)

what reagent removes the carbonyl from a ketone?

Zn(Hg)/HClw

what reagent oxidizes an alkylbenzene (PhCH2CH3) to benzoic acid?

KMnO4, NaOH, H2O, heat

what reagent adds a bromine to the benzylic carbon on PhCH2CH3?

Br2 (or NBS)/uv

what reagent turns a NO2 into NH2?

Zn, Sn, or Fe/HClho

how do you make arenediazonium salts?

1. HNO3, H2SO4 (nitro group)

2. Zn, Hcl

3. OH (+2 = NH2 group)

   1. NaNO2, HCl (N2 group)

N2 + H3O, heat

-OH

N2 + CuCl (Br)

-Cl (Br)

N2+ HBF4 (KI)

-F (I)

N2+ H3PO2

-H

N2 + Ar’

N2-Ar’

what are the reagents for sulfunation?

SO3, H2SO4

what reagents are used for desulfonation?

H2O, H2SO4