Exam 2 OChem 2

Electron Donating substituents (EDG):

H, CH3, -OCH3, NR2

Electron Withdrawing substituents:

CN, Ketones, Esters, NO2, SO3H

Electron donating substituents are

ortho-para directors

Electron withdrawing substituents are

meta directors

Is the diene a nucleophile or an electrophile?

nucleophile; electron rich

Is the dienephile a nucleophile or an electrophile?

electrophile; electron poor

Sp2 hybridzed means 3 centers of electron denisty. T or F

T

How to determine non aromatic molecules?

if not in a “ring” or if double bonds are not connected

How to determine aromatic molecules?

Pi*e=4n+2, planar (more stable), n=2,6,10

How to determine anti aromatic molecules?

Pi*e=4n, non planar, n=0,4,8

Steps to do EAS mechanism:

1. generate good electrophile

2. have electrons (from double bond) grab onto floating halogen; may need to draw resonace structure

3. remove bond and have base (need to create it) remove hydrogen (regains pi bond)

4. final product

What does reagent Zn —> HCl do?

put an amine (NH2) on a benzene; have to go through nitation first

What reagent initiates nitration?

H2SO4

What does H30+ do?

remove blocking group (dil. H3O+) and adds OH

What does Zn(Hg) —> Cl do?

reduces ketones

The 1,4 addition is

the most stable, thermal product (100 degrees celcius), bromine on least substituted side

The 1,2 addition is

least stable, kinetic product, bromine on most substituted side of the double bond

What does the reagent SOCl2 do?

turns aldehyde into an acyl hailide (replaces OH with Cl)

What does reagent Br2; FeBr3 do?

adds bromine to benzene

What does reagent SO3; H2SO4 do?

sulfuric acid blocking group

What does reagent CO2 —> H3O+ do?

reacts with grignards to make carboxylic acids

What does reagent H2; Pt do?

reduces alkenes

Nitration must occur before a amine (NH2) is added. T or F

T

How do you get this electrophile? (Nitration)

Use H2SO4 (sulfuric acid) to protonate OH group on NO3 molecule to make water; push out arrow to make H2O the leaving group