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Organic Chemistry Reaction Mechanisms Flashcards

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1
Q

Alkene/-yne, H2, Pt / Ni

A

Hydrogenation. Syn addition of hydrogens on alkene or alkyne carbons. Fully reduces substrate to alkane.

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2
Q

Alkene/-yne, HX

A

Hydrohalogenation. Syn, Markovnikov addition of a hydrogen and halogen on alkene or alkyne carbons.

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3
Q

Alkene, H2O, acid

A

Acid-catalyzed hydration. Markovnikov addition of a hydrogen and hydroxyl on alkene carbons.

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4
Q

Alkyne, H2O, acid, HgSO4

A

Acid catalyzed hydration. Markovnikov addition of a hydrogen and hydroxyl on alkyne carbons. Further reactions with acid create ketones.

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5
Q
  1. Alkene, BH3, THF / 2. H2O2, NaOH
A

Hydroboration-oxidation. Syn, anti-Markovnikov addition of a hydrogen and hydroxyl on alkene carbons.

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6
Q
  1. Alkyne, BH3, THF / 2. H2O2, NaOH
A

Hydroboration-oxidation. Syn, anti-Markovnikov addition of a hydrogen and hydroxyl on alkene carbons. Further reactions with base create aldehydes.

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7
Q

Alkene, X2, CCl4

A

Halogenation. Anti, Markovnikov addition of halogens on alkene carbons.

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8
Q

Alkene, X2, H2O

A

Halohydrin synthesis. Anti, Markovnikov addition of a halogen and hydroxyl on alkene carbons.

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9
Q
  1. Alkene, RCO3 / 2. H3O+
A

Anti-dihydroxylation. Anti, Markovnikov addition of hydroxyl groups on alkene carbons.

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10
Q
  1. Alkene, OsO4 / 2. Proton
A

Syn-dihydroxylation. Syn, Markovnikov addition of hydroxyl groups on alkene carbons.

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11
Q

Alkene, KMnO4, Heat

A

Alkene breaker. Creates ketones or carboxylic acids.

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12
Q
  1. Alkene, O3 / 2. DMS
A

Ozonolysis. Alkene breaker. Creates ketones or aldehydes.

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13
Q
  1. Alkyne, O3 / 2. DMS
A

Ozonolysis. Alkyne breaker. Creates carboxylic acids. If terminal alkyne, also creates carbon dioxide.

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14
Q

Dihalide alkane, NaNH2, NH3

A

Alkyne preparation using dihalide alkanes. Proceeds via E2 elimination.

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15
Q

Alkene/-yne, H2, Lindlar Pd

A

Hydrogenation. Syn addition of hydrogens on alkene or alkyne carbons. Reduces alkynes to alkenes.

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16
Q

Alkene/-yne, Na, NH3

A

Anti addition of hydrogens on alkene or alkyne carbons. Reduces alkynes to alkenes.

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17
Q
  1. Alkyne, NaNH2 / 2. RX
A

Alkyne addition. Replaces halogen on R group with alkyne

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18
Q
  1. Ketone/aldehyde, NaBH4 / 2. Proton
A

Alcohol preparation. Reduces ketones or aldehydes into alcohol without affecting substitution.

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19
Q
  1. Carbonyl, LiAlH4 / 2. Water
A

Alcohol prepartion. Reduces carbonyls into alcohols. Ester and carboxylic acid breaker.

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20
Q

Alkyl halide, Mg, Et2O

A

Grignard reagent formation. Perfect substrate for alcohol formation. Very reactive product.

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21
Q
  1. Carbonyl, Grignard reagent, Et2O / 2. H3O+
A

Alcohol preparation. Reduces carbonyls into alcohols and adds Grignard R group onto alcohol carbon. Reactive nature of Grignard reagent breaks esters or carboxylic acids

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22
Q

Secondary alcohol, Na2Cr2O7, H2SO4, H2O

A

Ketone preparation. Oxidizes secondary alcohols into ketones.

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23
Q

Primary alcohol, Na2Cr2O7, H2SO4, H2O

A

Carboxylic acid preparation. Oxidizes primary alcohols into carboxylic acids.

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24
Q

Alcohol, PCC

A

Carbonyl preparation. Prepares aldehydes if alcohol is primary.

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25
Alcohol, TBDMS-Cl
Alcohol protection. Alcohol can be restored with TBAF and H3O+
26
Alcohol, TsCl, pyrimidine
Tosylate preparation. Creates the perfect leaving group for SN2 reactions.
27
Alcohol, MsCl, triethylamine
Methylate preparation. Creates the perfect leaving group for SN2 reactions.
28
Alcohol, HNO3, H2SO4
Nitrate ester preparation. Replaces hydroxyl group with nitrate.
29
Prim/Sec alcohol, SoCl2, pyrimidine
Alkyl chloride preparation. Proceeds via SN2 mechanism.
30
Prim/Sec alcohol, PBr3
Alkyl bromide preparation. Proceeds via SN2 mechanism.
31
1. Alcohol, strong base / 2. RX
Williamson ether synthesis. Creates ether via SN2 mechanism.
32
Ether, excess HX, heat
Acidic cleavage of ether. Creates alkyl halides from ether constituents; may also create an alcohol if it is stable enough.
33
1. Epoxide, strong nucleophile / 2. Proton
Epoxide ring opening. Anti, anti-markovnikov addition of nucleophile relative to hydroxyl group. Initial reaction proceeds via SN2 mechanism.
34
Epoxide, protonated nucleophile, proton
Acid-catalyzed epoxide ring opening. Anti, markovnikov addition of nucleophile relative to hydroxyl group.
35
1. Thiol, strong base / 2. RX
Sulfide preparation. Creates sulfides via SN2 mechanism.
36
1. Diene / 2. Dienophile
Diels-Alder reaction. Creates Diels-Alder product. Endo conformation preferred; product may be predicted by "ionic" interactions.
37
Benzene, X2, AlX3/FeX3
Benzene halogenation. Substitute one hydrogen for a halogen.
38
Benzene, NO3, H2SO4
Benzene nitration. Substitute one hydrogen for a nitro group.
39
1. Nitrobenzene, Fe/Sn, HCl / 2. NaOH
Nitrobenzene amination. Substitute nitro group for an amine group.
40
Benzene, H2SO4
Benzene sulfonation. Substitute one hydrogen for a sulfurous acid group. Equilibrium reaction with water as a product.
41
Benzene, SO3, H2SO4
Benzene sulfonation. Substitute one hydrogen for a sulfurous acid group.
42
Benzene, RX, AlX3
Friedel-Craft alkylation. Substitute one hydrogen for the R group. Favors substitution with the most stable carbocation.
43
Benzene, R-acyl-X, AlX3
Friedel-Craft acylation. Substitution one hydrogen for the acyl-R group; acyl is closest to benzene.
44
Benzene, Na, NH3, ROH
Birch reduction. Creates a cyclohex-1,4-diene.
45
EWG-benzene, Na, NH3, ROH
Birch reduction. Creates a 3-EWG-cyclohex-1,4-diene.
46
EDG-benzene, Na, NH3, ROH
Birch reduction. Creates a 1-EDG-cyclohex-1,4-diene.
47
Alkyl benzene, NBS, heat
Free radical bromination. Attaches a bromine to a benzylic carbon.
48
Benzyl bromide, Nucleophile, Solvent
Benzyl bromide substitution reaction. Proceeds via SN1 or SN2 based on reagents.
49
Alkyl benzene, Na2Cr2O7, Proton, Heat
Benzoic acid preparation. Converts benzylic carbon into a carboxylic acid group.
50
Benzene w/ oxidized R group, Zn(Hg), HCl, H2O
Clemmensen reduction. Completely reduces the R group.
51
Benzene orthro/para disubstituted w/ EWG and leaving group, Nucleophile, Solvent
Nucleophilic aromatic substitution. Substitutes the leaving group for the nucleophile, conditions permitting.
52
Halobenzene, NH2, NH3 (l)
Aniline preparation. Adds ortho to or replaces halide leaving group.
53
1. Halobenzene, NaOH, heat / 2. Proton
Phenol preparation. Adds ortho to or replaces halide leaving group.
54
Aldehyde/ketone, H2O
Geminal hydrate preparation. Converts carbonyl into geminal diol.
55
Aldehyde/ketone, ROH
Hemiacetal preparation. Converts carbonyl into an alcohol-ether hybrid. May occur within the same molecule if aldehyde/ketone and alcohol are present to form cycllic compounds (as in carbohydrates).
56
Aldehyde/ketone, acid, H2O
Acid-catalyzed hydration. Converts carbonyl into geminal diol.
57
Aldehyde/ketone, base, H2O
Base-catalyzed hydration. Converts carbonyl into geminal diol.
58
Aldehyde/ketone, ROH, acid
Acetal preparation. Converts carbonyl into carbon with two ether attachments. May occur within the same molecule if carbonyl and alcohol substituents are present.
59
Acetal, Acid, Water
Converts acetals into ketones/aldehydes.
60
Aldehyde/ketone, SH, acid
Thio-acetal preparation. Converts carbonyl into carbon with sulfide attachments. May occur within the same molecule if carbonyl and thiol substituents are present.
61
Aldehyde/ketone, primary/lone amine, proton
Imine preparation. Replaces carbonyl oxygen with imine. Equilibrium reaction that produces water in the forward reaction.
62
Aldehyde/ketone, secondary amine, proton
Enamine preparation. Replaces carbonyl oxygen with secondary amine and creates an alkene.
63
Aldehyde/ketone, hydroxyl amine, proton
Oxime preparation. Replaces carbonyl oxygen with hydroxyl amine.
64
Aldehyde/ketone, hydrazine, proton
Hydrazone preparation. Replaces carbonyl oxygen with hydrazone.
65
Aldehyde/ketone, KCN, proton
Carbon nucleophile attack. Oxidizes carbonyl carbon into an alcohol with cyanide attachment.
66
1. Aldehyde, Ag+, -OH, NH3 / 2. Proton
Aldehyde oxidation using Tollens' reagents. Reduces aldehyde into a carboxylic acid.
67
Aldehyde, Na2Cr2O7, H2SO4, H2O
Carboxylic acid preparation. Reduces aldehyde into a carboxylic acid.
68
1. Carboxylic acid, BH3, THF / 2. Proton
Alcohol preparation. Selectively reduces carboxylic acids into primary alcohols.
69
Carboxylic acid, SOCl2, pyrimidine
Acyl chloride preparation. Forward reaction produces SO2 and HCl.
70
1. Carboxylic acid, NaOH / 2. Acyl chloride
Acid anhydride preparation.
71
Carboxylic acid (≥2n), heat
Acid anhydride preparation by dehydration. Mostly works for acetic acid.
72
Carboxylic acid, ROH, proton
Fischer esterification. Can occur within the same molecule if carboxylic acid and alcohols are both present.
73
Carboxylic acid, DCC, Amine
Amide preparation.
74
Carboxylic acid, ketone, heat
Enol preparation / decarboxylation. Converts ketone carbonyl into an alcohol and carboxylic acid into CO2.
75
Ester, water
Ester hydrolysis. Produces carboxylic acid and an alcohol.
76
Amide, acid, heat
Amide hydrolysis. Creates carboxylic acid and ammonia.
77
1. Amide, NaOH / 2. Proton
Amide hydrolysis. Creates carboxylic acid and ammonium.
78
Aldehyde(s), NaOH, H2O
Aldol addition. Reaction reduces some of the aldehyde alpha carbons (kinetics dependent on stereochemistry of substrates), which then react with other aldehydes to create an aldol.
79
Aldehyde(s), NaOH, H2O, heat
Aldol condensation. Heat reaction creates an enal from the aldol that would form normally.
80
Aldol/enal, NaCO3
Enal breaker at the alkene. Produces two aldehydes.

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