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42 Terms

1
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Secondary Alcohols to Ketones

NaOCl/H2O or Na2Cr2O7/H2SOâ‚„; DMP reagent, PCC, Swern oxidation

2
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Primary Alcohols to Carboxylic Acids

Excess NaOCl/TEMPO or Na2Cr2O7/H2SO4

3
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Primary Alcohols to Aldehydes

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

4
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Alkene to ketone

O3 and (CH3)2S

5
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Hydration of Alkynes

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

6
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Ketones through cuprates

R2CuLi+ acid chloride=ketone

7
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diol formation from ketone

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

8
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Wittig reaction

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

9
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Converts ketones or aldehydes to cyanohydrins

Reagents: Hydrogen cyanide (HCN)

10
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Imine formation

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

11
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Enamine formation

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

12
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Formation of acetal

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

13
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Hemiacetal

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

14
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Hydrolysis of Acetals

Adding water to acetal will bring it back to original ketone

15
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Cyclic acetals

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

16
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Acetals protecting group

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

17
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Ketones to secondary alcohols/ aldehydes to primary alcohols

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

18
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Catalytic Hydrogenation

Reduces both alkene and carbonyl, use Ni-H2

19
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Wolf-Kishner reduction vs clemmenson reduction

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

20
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Pyridine aromatic reactions

Does nucleophilic substitution ortho and para; EAS is meta.

21
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Alkylations of Amines

Excess Nh3 is needed to produce primary amines

22
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Acylation of amines

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

23
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Amines as leaving groups

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

24
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Nitrile to ketone

Grignard+ H3O+

25
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Based catalyzed resonance enolate

Add OH- to ketone, forms enol

26
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acid based catalyzed tautomerism

Forms enol again

27
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Quantitative enolate formation

ketone+LDA= enol

28
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Base-promoted alpha halogenation of ketones

X2 and OH-, adds two halogens to carbon

29
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Haloform reaction

Ketone, xs X2, OH- forms carboxylate ion

30
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acid catalyzed hydrogenation

ketone, Br2 and CH3COOH just adds halogen to ketone

31
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Alkylations of enolates

LDA then attacks alkyl halide to add R group

32
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kinetic vs thermodynamic enols

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

33
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Alkylation of aldehyde thru imine

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

34
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alkylating through enamine

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

35
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Alkylation of enamine

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

36
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Acylation of Enamines

Add acyl chloride to make diketone

37
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aldol condensation

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

38
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Aldol cyclization

diketones intramolecularly form a ring with a double bond

39
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CLAISEN CONDENSATION

ester enolate undergoes nucleophilic acyl substitution

40
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DIECKMANN CONDENSATION

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

41
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Malonic ester synthesis

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

42
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Michael reaction

conjugated addition with double bonds between carbons and carbonyl