im fucked

Secondary Alcohols to Ketones

Secondary Alcohols to Ketones

NaOCl/H2O or Na2Cr2O7/H2SO₄; DMP reagent, PCC, Swern oxidation

Primary Alcohols to Carboxylic Acids

Excess NaOCl/TEMPO or Na2Cr2O7/H2SO4

Primary Alcohols to Aldehydes

Controlled oxidation with PCC, DMP reagent, Swern, NaOCl/Tempo

Alkene to ketone

O3 and (CH3)2S

Hydration of Alkynes

Hg+, H2SO4, H2O ADDS OH GROUP DOUBLE BOND, THEN TAUTOMERIZES TO KETONE

Ketones through cuprates

R2CuLi+ acid chloride=ketone

diol formation from ketone

ketone+h2o= geminal diol (Can be done with either H3O+ or OH-)

Wittig reaction

Ketone to alkene by adding P(Ph)3-R, cleaves C=O bond and adds ylide to the ketone

Converts ketones or aldehydes to cyanohydrins

Reagents: Hydrogen cyanide (HCN)

Imine formation

ketone/aldehyde+Z-nh2= Z-N=C-(two groups originally on ketone)

Enamine formation

ketone plus R2NH/H+/h2o=> C=C-nr2

Formation of acetal

aldehyde/ketone+ 2R"-OH with H+ catalyst

Hemiacetal

OH and O-R group is on carbon, formed by adding ROH to ketone

Hydrolysis of Acetals

Adding water to acetal will bring it back to original ketone

Cyclic acetals

aldehyde+diol produces a cyclic acetal on the carbon originally double bonded to O

Acetals protecting group

Can protect groups, aldehydes are more reactive, taken off with H+

Ketones to secondary alcohols/ aldehydes to primary alcohols

NaBH4; DOES NOT REDUCE ESTERS, CARBOXYLIC ACIDS, ACYL CHLORIDES, OR AMIDES!

Catalytic Hydrogenation

Reduces both alkene and carbonyl, use Ni-H2

Wolf-Kishner reduction vs clemmenson reduction

Wolff-Kishner reduction can reduce acetals, clemmenson can't

Pyridine aromatic reactions

Does nucleophilic substitution ortho and para; EAS is meta.

Alkylations of Amines

Excess Nh3 is needed to produce primary amines

Acylation of amines

After acylation, the acyl group can be taken off with H3O+ or OH-

Amines as leaving groups

Elimination reactions from exhaustive methylation, common reagents are CH3I and Ag2O

Nitrile to ketone

Grignard+ H3O+

Based catalyzed resonance enolate

Add OH- to ketone, forms enol

acid based catalyzed tautomerism

Forms enol again

Quantitative enolate formation

ketone+LDA= enol

Base-promoted alpha halogenation of ketones

X2 and OH-, adds two halogens to carbon

Haloform reaction

Ketone, xs X2, OH- forms carboxylate ion

acid catalyzed hydrogenation

ketone, Br2 and CH3COOH just adds halogen to ketone

Alkylations of enolates

LDA then attacks alkyl halide to add R group

kinetic vs thermodynamic enols

kinetic-low temperature, less substituted side, thermodynamic product is more substituted side

Alkylation of aldehyde thru imine

Add r-nh2, turns aldehyde into imine, then react with CH3Br and H3O+ to return to aldehyde

alkylating through enamine

react ketone with secondary amine to form enamine, add Ch3Br, cleave double bond to N with H3O+

Alkylation of enamine

enamine+R-X, H3O+= longer ketone chain

Acylation of Enamines

Add acyl chloride to make diketone

aldol condensation

alpha, carbon attacks carbonyl and goes thru e2 reaction to make double bond

Aldol cyclization

diketones intramolecularly form a ring with a double bond

CLAISEN CONDENSATION

ester enolate undergoes nucleophilic acyl substitution

DIECKMANN CONDENSATION

INTERNAL CLAISEN ATTACK, KICKS OUT ESTER GROUP AND FORMS BOND WITH ALPHA CARBON

Malonic ester synthesis

NaOC2H5, R-X, R group added to alpha carbon between two ester groups

Michael reaction

conjugated addition with double bonds between carbons and carbonyl