O-Chem Reaction Mechanisms

Front 1

BH3 / O2H2 OH-

Back 1

nonmarkovnikov addition of H2O

In alkynes (if terminal) creates an aldehyde

Front 2

Hg(OAc)2, BH3/THF / NaBH4

Back 2

Markovnikov addition of H2O

Front 3

H2 / Pd/C in ethanol or PtO2

Back 3

reduces double bonds, syn stereochemistry

Front 4

OsO4/NMO

Back 4

Adds OH to both sides, syn stereochemistry

Front 5

O3/Zn,H3O+

Back 5

C=C is cleaved, O= added to both carbons

One ketone and one aldehyde

Front 6

KMnO4/H3O+

Back 6

C=C is cleaved, creates carboxylic acid (if one carbon has 2 hydrogens, CO2 is formed)

Front 7

HIO4/H20 THF

Back 7

2 -OH groups in an open chain --> 2 carbonyl compounds result

2 -OH groups in a ring, open ring diketone forms

Front 8

CHCl3/KOH

Back 8

Creates a carbene

stereospecific

Front 9

X2/H2O

Back 9

Markovnikov regiochemistry

Antistereochemistry

Front 10

KOH / ethanol

Back 10

dehydrohalogenation, forms double bond

Front 11

H2SO4, H2O / THF (50deg)

Back 11

dehydration, forms double bond

Front 12

H2O, H2SO4 / HgSO4

Back 12

Hydration of alkyne, occurs with Markovnikov regiochemistry

Ketone more favored than enol

Front 13

BH3, THF / H2O2, H2O, NaOH

Back 13

hydroboration-oxidation

if on terminal alkyne, creates an aldehyde

Front 14

H2 / Lindlar Catalyst

Back 14

syn reduction of alkyne

cis alkene product

Front 15

Li / NH3

Back 15

anti reduction of alkyne

trans alkene product

Front 16

NaNH2, NH3 / RX

Back 16

alkyne alkylation

Front 17

SOCl2 / Pyridine

Back 17

Converts primary/secondary alcohols into alkyl halides -- SO2 and HCl form

Front 18

PBr3 / ether 35C

Back 18

Converts primary/secondary alcohols into alkyl halides -- H3PO3 forms

Front 19

HF / Pyridine

Back 19

Forms alkyl fluoride on alcohols -- replaces the OH with an F :)

Front 20

HX + tertiary alcohol

Back 20

converts alcohol to alkyl halide -- reactivity order: 3>2>1

Front 21

NBS / hv CCl4

Back 21

makes alkyl halide from alkene by allylic bromination

Front 22

Mg / Ether

Back 22

Formation of grignard (organomagnesium) reagents

kinda pops the X off of the end and adds an - Mg - X

Front 23

R--X --2 Li / Pentane--> R--Li + LiX

and Ether --> [R-Cu-R]- Li+ + LiI

Back 23

Formation of diorganocopper reagents

Front 24

B(OH)2 + I --Pd(PPh3)4/CaCO3,THF -->

Back 24

They bond together

Front 25

SN1 reaction of 3d allylic and benzylic halides

Back 25

--X -->:Nu- --> --Nu + :X-

mostly primary (RCH2X)

Front 26

SN2 Reaction of 1d and simple 2d halides

Back 26

Nu --C + X:-

Mostly secondary (R2CHX)

Front 27

E1 reaction

Back 27

halide leaves, double bond b/t carbons halide was on

Front 28

E1cB Reaction

Back 28

With a base, same as E1 reaction basically

Front 29

E2 reaction

Back 29

Base: + KOH / Ethanol produces double bond b/t carbons