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Chem 239 reagents > Chem 239 Reactions > Flashcards

Chem 239 Reactions Flashcards

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1
Q

Oxidation of alcohols

A

weak: to ketone, PCC
strong: to COOH, KmnO4

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2
Q

Alkylbenzenes

A

to alkylate: R-Cl with AlCl3

To add carboxylic acid: KMnO4/H+

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3
Q

Grignard with Co2

A

Brominate benzene with Br2/FeBr3, remove Br with Mg, add CO2 and H3O+

Forms carboxylic acid

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4
Q

Acid chloride synthesis

A

SOCl2 or PCl5, COOH to COCl

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5
Q

Amide synthesis

A
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6
Q

Anhydride synthesis

A

Two carboxylic acids + heat

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7
Q

Decarboxylation reaction

A
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8
Q

Acid catalyzed esterification

A

carboxylic acid + R-OH-> Ester

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9
Q

Carboxylic acid reduction

A
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10
Q

Ester hydrolysis

A

RCOOR+H3O+->COOH

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11
Q

Lactonization

A

H+

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12
Q

Saponification

A

Ester-> carboxylic acid with carboxylate intermediate

Reagent: NaOH, then H+ workup

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13
Q

Acid catalyzed transesterificstion

A
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14
Q

Amide hydrolysis

A

H2O

amide> carboxylic acid

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15
Q

Acid chloride hydrolysis

A

H2O

acid chloride-> carboxylic acid

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16
Q

Ester reduction

A

LiAlH4

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17
Q

Amide reduction

A

LiAlH4+

RCONH2->R-NH2

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18
Q

Reaction of esters with grignard

A

ester->

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19
Q

Keto enol tautomerizarion

A
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20
Q

Acid catalyzed enolization

A

H3O+

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21
Q

Base catalyzed enolization

A

OH-

22
Q

Malonic ester synthesis

A

Use NaOet and r-Br group of choice to turn a-carbon into nucleophile

23
Q

Acetoacidic ester synthesis

A

Use NaOet and r-Br

24
Q

Haloform reaction

A

excess X2, NaOH, , mild acidic workup

CHX3 formed, becomes leaving group

25
Q

Aldol condensation

A

Addition: NaOH, H2O
condensation: heat, creates alkene

26
Q

Intramolecular claisen

A

use NaOH

27
Q

Conjugate addition

A
28
Q

1,2/1,4 additions

A
29
Q

Michael addition

A

KOH, Alkene, H2O

OH deprotonates, carbanion attacks, H grabbed

30
Q

Robinson annulation

A

Start with Michael addition:
KOH, Alkene, H2O
OH deprotonates, carbanion attacks, H grabbed by alkene

Then: Base grabs a-hydrogen, intramolecular reaction, O- protonated and kicked off

31
Q

Gabriel synthesis

A

KOH

H2NNH2

32
Q

Reductive amination

A

H+, NaBH3CN

33
Q

Amines via reduction

A

Amide or nitrile-> amine using LiAlH4 and H3O+

34
Q

Hofmann elimination

A

R-NX3->alkene using Ag2O and heat

35
Q

EAS with arylamines

A

aniline + (CH3CO)2O/pyridine -> Acetanilide

36
Q

Nitrosations

A

No2 + HCl->N=O

N=O attacks NH2 on aryl amine

37
Q

Reactions with Aryl diazonium salt

A

Ph-NH2 w/ HNO2 and H+-> Ph-N=-N

38
Q

Mutarotation

A

Mechanism: H3O+ or OH- open hemiacetal, internal rotation of carbonyl, H3O+ or OH- closes hemiacetal

39
Q

Isomerization of aldoses/ketoses

A
40
Q

Glycosides

A

monosaccharides + alcohols in acid give cyclic acetals (one OH group->OCH3)
- to return to OH, use H3O+

41
Q

Ether and ester derivatives of carbohydrates

A
42
Q

Oxidation of carbs

A

Strong: HNO3 used, Turns first and last carbon to carboxylic acid
Weak: Br2, water, Turns CHO on top to carboxylic acid

43
Q

Reduction of carbs

A

NaBH4

turns top COH to CH2OH

44
Q

Epimerization

A

NaOH and H2O

45
Q

Killiani Ester Synthesis

A
  1. HCN
  2. H2, Pd/BaSO4
  3. H3O+

Just adds extra carbon

46
Q

claisen condensation

A

Two esters + EtOH/HCl

makes acetoacetic ester

47
Q

periodate oxidation

A

OH groups turned into aldehyde

48
Q

To turn diazonium into other things

A

CN: CuCN
Br: CuBr
Cl: CuCl

49
Q

To add NO2 group to benzene

A

HNO3 and H2SO4

50
Q

To turn nitro group into an amine

A

H2, Pd

51
Q

ketone to carboxylic acid

A

NaOH, Br2, H3O+

Chem 239 reagents (6 decks)

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