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organic chem > reagents > Flashcards

reagents Flashcards

(59 cards)

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1
Q

free radical halogenation

A

Br - more selective
Cl - less selective
and hv (light), heat, or ROOR (peroxide)

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2
Q

allylic/benzylic bromination

A

NBS and light/heat/peroxide
- forms at allylic carbon (carbon next to double bond)

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3
Q

diene addition

A

heat or light

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4
Q

side chain oxidation of benzene to form benzoic acid

A
  1. KMnO4, -OH
  2. H3O+, heat
  3. Na2Cr2O7
  4. H2SO4
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5
Q

clemmensen reduction

A

Zn(Hg), HCl, Heat
or H2/Pd,C
C=O to C=C
NO2 to NH2

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6
Q

wolff-kishner reduction

A

(NH2)2, -OH, heat
C=O to C=C

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7
Q

acetylation of aniline

A

acetic anhydride
aniline to acetanilide

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8
Q

nitration

A

1.HNO3
2. H2SO4

benzene to benzene with NO2

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9
Q

sulfonation

A
  1. SO3
  2. H2SO4

benzene to benzene with SO3H

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10
Q

chlorination

A

Cl2/FeCl3

benzene to chloride benzene

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11
Q

bromination

A

Br2/FeBr3

benzene to bromide benzene

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12
Q

friedel crafts alkylation

A

RCl/AlCl3

adds R to benzene
rearrangement possible

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13
Q

friedel crafts acylation

A

acyl chloride/AlCl3

adds acyl group to benzene
no rearrangement possible

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14
Q

formylation

A

CO, HCl/ AlCL3

adds aldehyde to benzene

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15
Q

diazonium salt formation

A

NaNO2,HCl

NH2 to N2

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16
Q

diazonimum salt to Br and Cl

A

CuBr and CuCl

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17
Q

diazonimum salt to CN

A

CuCN

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18
Q

diazonimum salt to I

A

KI

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19
Q

diazonimum salt to phenol

A

H3O+ or EtOH

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20
Q

diazonimum salt to F

A

HBF4

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21
Q

diazonimum salt to benzene

A

H3PO2

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22
Q

nucleophilic addition to aldehyde or ketone

A

Nucleophile/H3O+

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23
Q

addition of water to aldehyde or ketone

A

H2O/H3O+ or OH
forms a hydrate

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24
Q

base catalyzed addition of alcohol to an aldehyde or ketone forming hemi-acetal

25
acid catalyzed addition of alcohol to an aldehyde or ketone forming hemi-acetal
H3O+/ ROH
26
acid catalyzed addition of ethylene glycol to an aldehyde or ketone to form an acetal
H3O+ and acetal
27
addition of primary amine to aldehyde forming an imine
RNH2/H3O+
28
addition of secondary amine to an aldehyde or ketone forming an enamine
secondary amine/H3O+
29
reduction of an aldehyde to primary alcohol
1.NaBH4 2. H3O+ 1. LiALH4 2. H3O+
30
addition of grignard reagent to aldehyde or ketone
1.RLI or MgX 2. H3O+
31
witting reaction
RPPh3 C=O to C=R
32
michael addition to a,b unsaturated ketone
anhydride, CN, HNR2, HSR, R2CuLi
33
addition of grignard to CO2
1. CO2, ether 2. H3O+
34
fisher esterifcation
ROH/H3O+
35
saponification
H3O+ ester to carboxylic acid or acid chloride
36
reduction of acid chloride to primary alcohol
1. LiAlH4 2. H3O+
37
reduction of acid anhydride to primary alcohol
1. LiAlH4 2. H3O+
38
reduction of ester to primary alcohol
1. LiAlH4 2. H3O+
39
reduction of carboxylic acid to primary alcohol
1. LiAlH4 2. H3O+
40
reduction of amide to amine
1. LiAlH4 2. H3O+
41
hoffman rearrangement
1. Br2 2. NaOH
42
reduction of nitrile to an amine
1. LiAlH4 2. H3O+
43
addition of grignard reagent to an ester
1. 2 MgX, ether 2. H3O+
44
addition of grignard reagent to an acyl chloride
1. 2 MgX, ether 2. H3O+
45
addition of grignard reagent to a carboxylic acid
1. MgX, ether 2. H3O+
46
addition of grignard to amide
1. MgX, ether 2. H3O+
47
addition of grignard to nitrile
1. MgX, ether 2. H3O+
48
acid catalyzed hydrolysis of nitrile
H3O+ and heat
49
SN2 formation of nitriles using cyanide and alkyl halides
-CN
50
cyanohydrin formation using aldehydes/ketones and cyanide
-CN
51
suzuki reaction
PdL2, OH R-X + RBOR -> R-R
52
heck reaction
R-X + allylic carbon = R bonded to allylic carbon PdL2/ Et2N
53
reductive amination
1. NH2-R 2. H2/PdC ketone to imine to amine
54
hydrogenation alkyl azides
NaN3/H2 R-Br to R-CN to R-CH2-NH2
55
nucleophilic aromatic substition
replace benzylic H with NH2
56
adding cyanide to aldehydes and ketones
NaCN/HCN
57
acid catalyzed hydrolysis of nitrile
H3O+/heat
58
acid chloride to amine
NH2-R or H
59
addition of primary amine to aldehyde or ketong forming imine
NH2R/H3O+

organic chem (14 decks)

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