Organic Chemistry Exam 3

Halolkane

C-X

Ketone

O=C(-C)

Aldehyde

O=C-H

Carboxylic Acid

O=C-O-H

Ester

O=C-O-C

Amide

O=C-N

Amine

C-N

Ether

C-O-C

Alcohol

C-O-H

F

Fluoro

I

Iodo

Cl

Chloro

Br

Bromo

Alcohol Suffix

-ol

Common Good LG (More Basic)

I>Br>Cl; O+R2, OSO2R (OTs, OMs)

Common Good Nucleophiles (Less sterically crowded, stronger bases)

Br⊖, CN⊖, N3⊖, I⊖, ⊖SH, ⊖SR, ⊖OH, ⊖OR

Common Average Nucleophiles

NH3, Cl⊖, RCO2⊖

Common Poor Nucleophiles

H2O, ROH (CH3OH or MeOH, EtOH or CH3CH2OH), CH3COOH (AcOH), HSO4⊖

Common Protic Solvents (Anions)

H2O, CH3OH(MeOH), EtOH (CH3CH2OH), CH3COOH (AcOH) (Contains OH)

Common Aprotic Solvents (Metals)

DMF, DMSO, acetone, acetonitrile

Double Bonds

changes ending from an to en, add number of start of bond

E/Z

e is trans z is cis

Me

SN2 only

1

SN2 and E2 possible

3

E2 very fast with a strong base (E1: + H2SO4) (E2: + POCl3, Py)

2

E2 fast with a strong base, but all mechanisms possible (SN2+ SN1: + HCl, HBr, HI) (SN2: + PBr3, SOCl2) (E1: + H2SO4) (E2: + POCl3, Py)

vinylic

E2 possible

Weak Base

E2 Slow

Strong Base

E2 Speeds Up

Poor nucleophile

SN2 very slow

Good Nucleophile

SN2 speeds up

Not Polar

SN1/E1 slow down; SN2 and E2 less so

Polar Aprotic

SN2 speeds up more than SN1

Polar Protic

SN1

Vinylic

one of the two atoms that form the double bond

Allylic

carbon atom that is next to the double-bonded carbon atom