Organic Chemistry

Front 1

Hydroboration

Back 1

1)Other reagents: BH3 in THF or B2H6

2) Other Bases: KOH

Front 2

Oxymercuration

Back 2

Goes Through 3-memberd "mercurinium" ion. NaBH4 step removes the mercury.

If -OH is used instead of H2O an ether will form.

Front 3

Acid-catalyzed addition of H2O (Hydration)

Back 3

Front 4

Addition of HX

Back 4

Also HI

Front 5

1)Bromination

2)Halohydrin Formation

Back 5

Water and alcohol solvents will for halohydrin but all others (CCl4, CHCl3, hexane) will give dibromide

Intermediate is a bromide bonded to both C

Front 6

Chlorination

Back 6

Halohydrin is formed if water or alcohol is used as solvent

Front 7

Epoxidation

Back 7

m-CPBA is commonly used for RCO3H

If H3O+, heat is added then epoxide is opened to give diol

Front 8

Dihydroxylation

Back 8

1) Ocasioanlly a second reagent such as NaHSO3, H2S, or NA2S2O3 is used as a recant in the reaction

2) If heat or acid is mentioned the idol will be cleaved to form carbonyl compound

Front 9

Hydrogenation

Back 9

Other metal catalysts include: Pt or Ni

Front 10

Radical Addition of HBr

Back 10

Front 11

Ozonolysis

Back 11

Reductive: Zn or DMS is used to reduce to isolate aldehyde

Oxidative: H2O2 is used to obtain carboxylic acid instead of aldehyde (can also use KMnO4 and acid)

Front 12

Cyclopropanation

Back 12

Can also use CHCl3, NaOH

Front 13

Reductive Workup Mechanism

Back 13

Front 14

Oxidative Workup

Back 14

Front 15

3- Membered ring pathway (Br2/H2O2 to alkene)

Back 15

Front 16

Elimination of Hydrogen Halides

Back 16

Most substituted alkyne will form

Front 17

Deprotonation

Back 17

Can also use strong base like n-BuLi, or RMgBr (Grignard reageants)

Front 18

Reaction with Electrophile

Back 18

will react with alkyl halides in SN2 rxns

Front 19

Hydrogenation

Back 19

Pt, Ni, Rh also can be used to go from alkyne to alkane

Front 20

Partial Hydrogenation/

Back 20

creates a cis-alkene through use of Pd, CaCO3

Front 21

Metal Ammonia Reduction

Back 21

Creates a trans-alkene

Front 22

1) Addition of Hydrogen Bromide

2) Addition of Hydrogen Chloride

Back 22

A vinyl carbocation is formed as an intermediate in these creations.

Front 23

Hydroboration

Back 23

Hydrboration on internal alkynes will give a mixture of ketones

Front 24

Acid Catalyzed Hydration

Back 24

Tautomerization converts alkene into aldehyde/ketone

Front 25

Oxymercuration

Back 25

The first intermediate is a cyclic ion (triangle between Hg and multi bond.

Front 26

Chlorination

Back 26

First intermediate cyclic ion. First addition is trans

Front 27

Ozonolysis

Back 27

If R=H then one product will be CO2

Front 28

Bromination

Back 28

First intermediate is cyclic ion. First addition is trans.