Chem 215 - Exam 1

Jones

- creates carboxylic acids

Carboxylic acid

-forms from primary alcohols with water

Aldehyde

- forms from primary alcohols without water

ketone

-forms from secondary alcohols

PCC

PDC

swern oxidation

Hydroboration

- anti-markonikov addition of H2O

Regio: anti-markonikov

Stereo: Syn

Adds: -OH and -H

Common reagents: BH3 or B2H6

Common solvent: H2O2, NaOH

Hydration

- markonikov addition of H2O

Regio: Markonikov

stereo: syn and anti

Adds: -OH and -H

Common reagents: H2O

Common solvents: H2SO4

Halogenation

• anti-addition reaction

Regio: none

stereo: anti

adds: Br2, Cl2, I2, F2, etc.

Halohydrin

• anti-additon reaction

• regio: none

• stereo: anti

• adds: -OH and -X

• common reagents: Br2+H2O , NBS + H2O, Br2+ROH, NBS + ROX

Hydrohalgenation

-addition to alkene

regio: Markonikov

stero: syn and anti

adds: -H and -X

Common reagents: HCl, HBr, HI

Dihydroxylation

Regio: none

stereo: syn

adds: -OH and -OH

Reagent: OSO4 or KMnO4

2nd step: NaOH,H2O or Na2SO3,H2O

Ozonolysis

Regio: none

Stereo: syn

common reagent: 1. O3

Common solvents: 2. Zn or 2.H2O2 or CH3CH3S

Epoxidation

regio: none

stereo: syn

common reagent: RCOOOH

Hydrogenation

- reduction reaction

regio: none

stereo: syn

adds: -H and -H

common reagent: H2

common solvent: Pd/ C

alkynes: H2 will add until fully saturated

Poised Catalyst

-reduction reaction

regio: none

stereo: syn

adds: -H and -H

common reagent: H2

common solvent: pd/BaSO4 w Pbo OR pd/CaCO3 w pbo or quinaline

Dissolving Metal

-reduction reaction

regio: none

stereo: anti

adds: -H and -H

common reagents: Na,Li or K

Common solvent: NH3

Grignard

Ketone → tertiary alcohol

Aldehyde → secondary alcohol

Hydride nucleophile

Ketone → secondary alcohol

Aldehyde → primary alcohol

solvents for NaBH4: CH3OH, H3O+,

solvents for LiAlH4: H3O+, H2O

Organolithium

Ketone → tertiary alcohol

Aldehyde → secondary alcohol

Epoxide opening with weak nucleophiles

- nucleophile reacts to most substituted carbon

-examples: Br2 or H-Br

-H-Br forms alcohol

epoxide opening with strong/basic nucleophiles

-OCH3 reacts to least substituted carbon

-requires a workup (H3O+)

-example: NaOCH3/CH3OH

-forms alcohol

addition of weak nucleophiles to aldehydes

additon of weak reversible nucleophiles

specific acid catalyst mechanism

general acid catalyst mechanism

condensation reactions of hemis

condensation reaction of hemis mechanism via sn1

condensation reaction of hemiaminal

mechanism of condensation of hemiaminal

hydrolysis reactions

mechanism of hydrolysis

intramolecular substitution reactions