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DAT > Organic Chemistry Reaction Mechanisms > Flashcards

Organic Chemistry Reaction Mechanisms Flashcards

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
Q

Alcohol, TBDMS-Cl

A

Alcohol protection. Alcohol can be restored with TBAF and H3O+

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26
Q

Alcohol, TsCl, pyrimidine

A

Tosylate preparation. Creates the perfect leaving group for SN2 reactions.

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27
Q

Alcohol, MsCl, triethylamine

A

Methylate preparation. Creates the perfect leaving group for SN2 reactions.

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28
Q

Alcohol, HNO3, H2SO4

A

Nitrate ester preparation. Replaces hydroxyl group with nitrate.

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29
Q

Prim/Sec alcohol, SoCl2, pyrimidine

A

Alkyl chloride preparation. Proceeds via SN2 mechanism.

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30
Q

Prim/Sec alcohol, PBr3

A

Alkyl bromide preparation. Proceeds via SN2 mechanism.

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31
Q
  1. Alcohol, strong base / 2. RX
A

Williamson ether synthesis. Creates ether via SN2 mechanism.

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32
Q

Ether, excess HX, heat

A

Acidic cleavage of ether. Creates alkyl halides from ether constituents; may also create an alcohol if it is stable enough.

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33
Q
  1. Epoxide, strong nucleophile / 2. Proton
A

Epoxide ring opening. Anti, anti-markovnikov addition of nucleophile relative to hydroxyl group. Initial reaction proceeds via SN2 mechanism.

34
Q

Epoxide, protonated nucleophile, proton

A

Acid-catalyzed epoxide ring opening. Anti, markovnikov addition of nucleophile relative to hydroxyl group.

35
Q
  1. Thiol, strong base / 2. RX
A

Sulfide preparation. Creates sulfides via SN2 mechanism.

36
Q
  1. Diene / 2. Dienophile
A

Diels-Alder reaction. Creates Diels-Alder product. Endo conformation preferred; product may be predicted by “ionic” interactions.

37
Q

Benzene, X2, AlX3/FeX3

A

Benzene halogenation. Substitute one hydrogen for a halogen.

38
Q

Benzene, NO3, H2SO4

A

Benzene nitration. Substitute one hydrogen for a nitro group.

39
Q
  1. Nitrobenzene, Fe/Sn, HCl / 2. NaOH
A

Nitrobenzene amination. Substitute nitro group for an amine group.

40
Q

Benzene, H2SO4

A

Benzene sulfonation. Substitute one hydrogen for a sulfurous acid group. Equilibrium reaction with water as a product.

41
Q

Benzene, SO3, H2SO4

A

Benzene sulfonation. Substitute one hydrogen for a sulfurous acid group.

42
Q

Benzene, RX, AlX3

A

Friedel-Craft alkylation. Substitute one hydrogen for the R group. Favors substitution with the most stable carbocation.

43
Q

Benzene, R-acyl-X, AlX3

A

Friedel-Craft acylation. Substitution one hydrogen for the acyl-R group; acyl is closest to benzene.

44
Q

Benzene, Na, NH3, ROH

A

Birch reduction. Creates a cyclohex-1,4-diene.

45
Q

EWG-benzene, Na, NH3, ROH

A

Birch reduction. Creates a 3-EWG-cyclohex-1,4-diene.

46
Q

EDG-benzene, Na, NH3, ROH

A

Birch reduction. Creates a 1-EDG-cyclohex-1,4-diene.

47
Q

Alkyl benzene, NBS, heat

A

Free radical bromination. Attaches a bromine to a benzylic carbon.

48
Q

Benzyl bromide, Nucleophile, Solvent

A

Benzyl bromide substitution reaction. Proceeds via SN1 or SN2 based on reagents.

49
Q

Alkyl benzene, Na2Cr2O7, Proton, Heat

A

Benzoic acid preparation. Converts benzylic carbon into a carboxylic acid group.

50
Q

Benzene w/ oxidized R group, Zn(Hg), HCl, H2O

A

Clemmensen reduction. Completely reduces the R group.

51
Q

Benzene orthro/para disubstituted w/ EWG and leaving group, Nucleophile, Solvent

A

Nucleophilic aromatic substitution. Substitutes the leaving group for the nucleophile, conditions permitting.

52
Q

Halobenzene, NH2, NH3 (l)

A

Aniline preparation. Adds ortho to or replaces halide leaving group.

53
Q
  1. Halobenzene, NaOH, heat / 2. Proton
A

Phenol preparation. Adds ortho to or replaces halide leaving group.

54
Q

Aldehyde/ketone, H2O

A

Geminal hydrate preparation. Converts carbonyl into geminal diol.

55
Q

Aldehyde/ketone, ROH

A

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
Q

Aldehyde/ketone, acid, H2O

A

Acid-catalyzed hydration. Converts carbonyl into geminal diol.

57
Q

Aldehyde/ketone, base, H2O

A

Base-catalyzed hydration. Converts carbonyl into geminal diol.

58
Q

Aldehyde/ketone, ROH, acid

A

Acetal preparation. Converts carbonyl into carbon with two ether attachments. May occur within the same molecule if carbonyl and alcohol substituents are present.

59
Q

Acetal, Acid, Water

A

Converts acetals into ketones/aldehydes.

60
Q

Aldehyde/ketone, SH, acid

A

Thio-acetal preparation. Converts carbonyl into carbon with sulfide attachments. May occur within the same molecule if carbonyl and thiol substituents are present.

61
Q

Aldehyde/ketone, primary/lone amine, proton

A

Imine preparation. Replaces carbonyl oxygen with imine. Equilibrium reaction that produces water in the forward reaction.

62
Q

Aldehyde/ketone, secondary amine, proton

A

Enamine preparation. Replaces carbonyl oxygen with secondary amine and creates an alkene.

63
Q

Aldehyde/ketone, hydroxyl amine, proton

A

Oxime preparation. Replaces carbonyl oxygen with hydroxyl amine.

64
Q

Aldehyde/ketone, hydrazine, proton

A

Hydrazone preparation. Replaces carbonyl oxygen with hydrazone.

65
Q

Aldehyde/ketone, KCN, proton

A

Carbon nucleophile attack. Oxidizes carbonyl carbon into an alcohol with cyanide attachment.

66
Q
  1. Aldehyde, Ag+, -OH, NH3 / 2. Proton
A

Aldehyde oxidation using Tollens’ reagents. Reduces aldehyde into a carboxylic acid.

67
Q

Aldehyde, Na2Cr2O7, H2SO4, H2O

A

Carboxylic acid preparation. Reduces aldehyde into a carboxylic acid.

68
Q
  1. Carboxylic acid, BH3, THF / 2. Proton
A

Alcohol preparation. Selectively reduces carboxylic acids into primary alcohols.

69
Q

Carboxylic acid, SOCl2, pyrimidine

A

Acyl chloride preparation. Forward reaction produces SO2 and HCl.

70
Q
  1. Carboxylic acid, NaOH / 2. Acyl chloride
A

Acid anhydride preparation.

71
Q

Carboxylic acid (≥2n), heat

A

Acid anhydride preparation by dehydration. Mostly works for acetic acid.

72
Q

Carboxylic acid, ROH, proton

A

Fischer esterification. Can occur within the same molecule if carboxylic acid and alcohols are both present.

73
Q

Carboxylic acid, DCC, Amine

A

Amide preparation.

74
Q

Carboxylic acid, ketone, heat

A

Enol preparation / decarboxylation. Converts ketone carbonyl into an alcohol and carboxylic acid into CO2.

75
Q

Ester, water

A

Ester hydrolysis. Produces carboxylic acid and an alcohol.

76
Q

Amide, acid, heat

A

Amide hydrolysis. Creates carboxylic acid and ammonia.

77
Q
  1. Amide, NaOH / 2. Proton
A

Amide hydrolysis. Creates carboxylic acid and ammonium.

78
Q

Aldehyde(s), NaOH, H2O

A

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
Q

Aldehyde(s), NaOH, H2O, heat

A

Aldol condensation. Heat reaction creates an enal from the aldol that would form normally.

80
Q

Aldol/enal, NaCO3

A

Enal breaker at the alkene. Produces two aldehydes.

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