Orgo 1 mechanisms based on reagants

SN2

-INVERSION OF STEREOCHEMISTRY

-POLAR APROTIC SOLVENTS(DMSO, DMF, MeCN, HMPA, etc)

- STRONG NUCLEOPHILES( X-, RS-, HS-, RSH-, H2S, CN-, N3-, weak bases)(OH-, MeO-, EtO-, RO-, strong bases)

- PRIMARY + SECONDARY

E2

-REGIOSELECTIVITY(zaitsev vs hofmann depending on reagent)

-STEREOCHEMISTRY

-ANTI-COPLANAR

-STRONG BASES(OH-, MeO-,EtO-,RO-, strong nucleophiles)(NaH, DBN, DBU, H-, weak nucleophiles)

-1-3 substituted for SB/WN, 2-3 major for SB/SN

SN1

-INVERSION OF STEREOCHEMISTRY

-POLAR PROTIC SOLVENT

-REARRANGEMENT

-NEUTRAL NUCLEOPHILES(X-, RS-,HS-,RSH-,H2S-CN-,N3-strong)(H2O,EtOH, CH3OH, Weak)

-HIGHLY SUBSTITUTED

E1

-NOT ANTI-COPLANAR

-REARRANGEMENT

-WEAK BASE/WEAK NUCLEOPHILE(H2O, MeOH, EtOH)

-HIGHLY SUBSTITUTED 3

-HEAT favors this reaction

hydrohalogenation

-markovnikov addition

-carbocation rearrangement

-racemic mixture if chiral center

reagent: HX

substrate: pi bond/alkene

acid-catalyzed hydration

-pi hond takes H from H3O+

-mark addition( OH2 to more sub), H2O removes H

-racemic mixture if chiral center

-amount of water(how dilute solution) determines direction of equilibrium

reagent: H3O+/H2SO4/H2O

substrate: pi bond/alkene

Hydroboration-Oxidation

-ANTI-mark addition( H to most and OH to least sub)

-synaddition(both wedge or dash)

reagents: 1) BH3, THF 2) H2O2, NaOH

substrate: pi bond/alkene

catalytic hydrogenation

-H on each side of Pi bond

-syn addition

reagent: H2 + Metal catalyst(Pt, Ni, Pd)

substrate: alkene

halogenation

-X added to both sides of the pi bond

-anti-addition

reagent:X2

substrate: alkene

halohydrin

-X and OH added across pi bond

-anti-addition

reagent: HO-X + H2O

substrate: alkene

anti dihydroxylation

-anti-addition of OH groups

reagents: RCO3H and H3O+

substrate: alkene

Syn Dihydroxylation

-syn-addition of OH groups across pi bond

reagents: 1) OsO4 and NMO or 2)KMnO4, NaOH, and cold

substrate: alkene

oxidative cleavage

-cleavage at pi bond and O attaches

reagents: O3 and H2O/DMS

substrate:alkene

catalytic hydrogenation

-H adds to bonds until alkane

reagents: H2 and metal catalyst

substrate: alkyne

poisoned hydrogenation

-cis alkene created

reagents:H2 and Lindlar's catalyst

substrate: alkyne

dissolving metal reduction

-trans alkene created

reagents:Na and NH3(l)

substrate: alkyne

hydrohalogenation

-mark addition

-alkene with 1 X group created

reagents: HX

substrate: alkyne

hydrohalogenation

-mark addition

-alkene with 2+ X groups created

reagents: excess HX

substrate: alkyne

hydrohalogenation

-anti-mark addition

reagents: HX and ROOR

substrate: alkyne

acid-catalyzed hydration

-mark addition(OH)

- produces a ketone(OH--> O)

reagents: 1) H2SO4, H2O 2)HgSO4

substrate:alkyne

hydroboration-oxidation

-anti mark addition

-aldehyde produced

reagents: 1)9-BBN and 2)H2O2, NaOH

substrate:alkyne

halogenation

-trans formation favored

- alkene with 2 X groups added

reagents: X2 and CCl4

substrate:alkyne

halogenation

-alkane with 4 X groups attached, two on each side of original triple bond

reagants: excess X2 and CCl4

substrate: alkyne