Reactions Chp 7 and Chp 8: Substitutions, Eliminations, and Additions of Alkenes

Starting Material: primary or secondary alkyl halides

Reagents: need a strong nucleophile (negatively charged, or electronegative)

Sn2 reaction

Products: backside attack of the nucleophile to the electrophile

Starting Material: primary and secondary alkyl with beta hydrogens and good leaving group

Reagents: strong base

E2 Reaction

Products: ALKENE FORMED

Starting Material:

Reagents: tertiary heat and weak base

E1 Reaction

Starting Material:

Reagents: HX, X = CL, BR, I

Hydrohalogenation (KNOW MECHANISM, CAN REARRANGE)

Products: MARK ADDN

Starting Material:

Reagents: HBR, ROOR

HYDRO-HALOGENATION WITH PEROXIDE

Products: ANTI-MARK ADDN OF BR (KNOW MECHANISM)

Starting Material:

Reagents: H3O+

ACID CATACLYZED HYDRATION (KNOW THE FIRST STEP )

Products: MARK ADDN OF OH; KNOW MECHANISM; CAN REARRANGE

Starting Material:

Reagents:

1) HG(OAC)2, H20

2) NABH4, NAOH

OXYMERCURATION-DEMUCURATION (KNOW THE FIRST STEP;SYN ADDN)

Products:MARK ADDN OF H AND OH

Starting Material:

Reagents:

1. BH3, THF

2. H2O2, NAOH

HYDROBORATION-OXIDATION

Products: ANTI MARK ADDN ADDS OH AND H (SYN)

Starting Material:

Reagents: H2, M, HIGH P

M=PD, PT, PH, NI

HYDROGENATION

Products: GETS RID OF ALKENE, SYN ADDN

Starting Material:

Reagents: X2, H2O

HALOGENATION

Products: ADDS TWO X GROUPS, KNOW MECHANISM, ANTI ADDN

Starting Material:

Reagents: X2, H2O

HALOHYDRIN

Products: ADDS A X GROUP AND OH GROUP, MARK ADDN, ANTI ADDN, KNOW MECHANISM

Starting Material:

Reagents:

KMNO4, NAOH, COLD

OR

1. OSO4

2. NA2SO3

OR

OSO4, NMO

OR

OSO4, ROOR

SYN-DIHYDROXYLATION

Products: ADDS TWO OH GROUPS, SYN ADDN

Starting Material:

Reagents: MCPBA OR RCO3H

EPOXIDATION

Products: ADDS O ACROSS DOUBLE BOND, SYN ADDN ONLY

Starting Material:

Reagents: H2SO4, H20 REACTS WITH AN EPOXIDE

ANTI-DIHDROXYLATION

Products: ADDS TWO OH GROUPS, SYN ADDN, KNOW MECHANISM

Starting Material:

Reagents:

1. O3

2. DMS OR ZN, H2O

OZONOLYSIS

Products: ADDS CARBONYLS; BREAKS THE BOND

Starting Material: tertiary alkyl halide

Reagents:

weak base

Sn1

products: OH added to the substrate