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Chem 14D Flashcards

1
Q

Hydroboration

A

Hydroboration:

Anti-Markovnikoff

syn addition

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2
Q

Oxymercuration

A

Oxymercuration:

Markovnikoff

syn + anti

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3
Q

Acid-catalyzed addition of H20 (hydration)

A

Acid-catalyzed addition of H20 (hydration):

Markovnikoff

syn + anti

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4
Q

Halogenation (Addition of HX)

HCl

A

Halogenation (Addition of HX):

Markovnikoff

syn + anti

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5
Q

Halogenation (Addition of HX)

HBr

A

Halogenation (Addition of HX):

Markovnikoff

syn + anti

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6
Q

Bromination (top reaction)

A

Bromination:

(Not Mark or Anti-Mark)

anti-addition

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7
Q

Halohydrin Formation (bottom reaction)

A

Halohydrin Formation (bottom reaction):

Markovnikoff

anti addition

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8
Q

Chlorination

A

Chlorination:

(not Mark. or anti-Mark.)

anti addition

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9
Q

Dihydroxilation

OsO4

A

Dihydroxialtion:

OsO4

(not Mark. or anti-Mark.)

syn addition

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10
Q

Dihydroxialtion:

KMnO4 (permanganate)

A

Dihydroxialtion:

KMnO4 (permanganate)

(not Mark. or anti-Mark.)

syn addition

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11
Q

Epoxidation

A

Epoxidation:

(not Mark. or anti-Mark)

syn addition

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12
Q

Hydrogenation

A

Hydrogenation:

(not Mark. or anti-Mark.)

syn addition

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13
Q

Radical addition of HBr

A

Radical addition of HBr:

Anti-Markovnikoff

syn + anti

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14
Q

Ozonolysis (Reductive workup, top reaction)

*bottom molecule can be S(Ch3)2 or Zn/H+

A

Ozonolysis (Reductive workup):

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15
Q

Ozonolysis (Oxidative workup, bottom reaction)

*can also use KMnO4 and acid

A

Ozonolysis (Oxidative workup):

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16
Q

Elimination of Hydrogen halides

*geminal dihalide

A

Elimination of Hydrogen halides

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17
Q

Elimination of Hydrogen halides

*vicinal dihalide

A

Elimination of Hydrogen halides

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18
Q

Hydrogenation (Addition Reactions fo Alkynes)

A

Hydrogenation (Addition Reactions fo Alkynes)

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19
Q

Partial Hydrogenation (Addition Reactions fo Alkynes)

A

Partial Hydrogenation (Addition Reactions fo Alkynes)

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20
Q

Addition of Hydrogen bromide (to form gem-dibromides)

A

Addition of Hydrogen bromide (to form gem-dibromides)

Markovnikoff

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21
Q

Addition of Hydrogen chloride (to form gem-dichlorides)

A

Addition of Hydrogen chloride (to form gem-dichlorides)

Markovnikoff

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22
Q

Bromination (Addition Reactions to Alkynes)

A

Bromination (Addition Reactions to Alkynes)

First addition is trans

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23
Q

Chlorination (Addition Reactions to Alkynes)

A

Chlorination (Addition Reactions to Alkynes)

First addition is trans

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24
Q

Deprotonation (Synthesis of Alkynes)

*Replace with Grignard: MgBr (molecule used in class)

A

Deprotonation (Synthesis of Alkynes)

*Replace with Grignard: MgBr (molecule used in class)

**Deprotonated alkyne makes excellent nucleophile

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25
Q

Good for making epoxides:

A

Percarboxylic acids

*Especially mCPBA (m-chloroperbenzoic acid)

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26
Q

Good for making diol:

A

Peracetic Acid with acidic H2O

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27
Q

True or False:

Warm, concentrated KMnO4 overoxidzes product and will not produce aldehydes, but instead carboxylic acids.

A

True

(Ex. diluted, basic, cold KMnO4 will produce vicinal diol from Z-alkene. Warm, concentrated KMnO4 will give carboxylic acid from Z-alkene)

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28
Q

Do internal alkynes have Markovnikoff or anti-Markovnikoff formations?

A

No, only terminal alkynes do.

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29
Q

Deprotonated terminal alkynes can do what type of reaction?

A

Sn2 (only 1°) - same reaction as a Grignard. Act as strong nucleophile.

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30
Q

True or False:

Grignards and Alkynes are incompatible.

A

True. Grignards will deprotonate Alkynes.

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31
Q

True or False:

H2 with a metal catalyst is a syn addition.

A

True.

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32
Q

True or False:

Hydrogenation of alkenes is a nonpolar process that requires a catalyst.

A

True

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33
Q

True or False:

Hydrogenation of alkenes generally proceeds via syn stereochemistry.

A

True.

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34
Q

True or False:

In very case of pericyclic reactions the products contain more σ (sigma) bonds and few pi bonds than the starting material.

A

True

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35
Q

True or False:

In pericyclic reactions stereochemical relationship in the starting materials are preserved through the reaction transition states and on into the products.

A

True

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36
Q

True or False:

The Dienophile has an electron withdrawing group which makes it relatiely electron-poor.

A

True

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37
Q

True or False:

The Diene has electron donating groups which makes it relatively electron-rich.

38
Q

True or False:

Alkynes can act as Dienophiles as well.

39
Q

Order from least to greatest in terms of electron-withdrawing strength:

CF3, Nitro Groups, Carbonyls (ketones, esters, aldehydes)

A

CF3 = Nitro Gropus (both strong) > Carbonyls (moderate)

*CF3 and Nitro have strong induction

40
Q

Are Friedel-Crafts Alkylations or Acylations better reactions and why?

A

Friedel-Craft Acylations are preferred because they don’t have rearrangements (like Alkylations) and there’s a low chance of multiple acylations.

41
Q

True or False:

Any carbocation can react with benzene.

42
Q

Hydrohalogenation (Alkene)

A

Hydrohalogenation (Alkene):

Addition of HX

Markovnikov

Rearrangements

43
Q

Hydration: Acid-catalyzed (Alkene)

A

Hydration: Acid-catalyzed (Alkene):

Markovnikov

Rearrangements

**lack of water gives dehydration - Elimination (E2, E1)

44
Q

Halogenation (Alkene)

A

Halogenation:

Anti-addition

*Bridged halonium ion intermediate

45
Q

Halohydrin (Alkene)

A

Halohydrin:

Anti-addition

Markovnikov for the –OH group

*Bridged halonium ion intermediate

(Attacked by water)

46
Q

Hydration: Oxymercuration-demercuration (Alkene)

A

Hydration: Oxymercuration-demercuration (Alkene):

Markovnikov

No rearrangments

47
Q

Hydroboration-oxidation (Alkene)

A

Hydroboration-oxidation (Alkene):

Syn addition

Anti-Markovnikov

48
Q

Dihydroxilation - Vicinal Diol (Alkene)

A

Dihydroxilation - Vicinal Diol (Alkene)

Syn stereochemistry

(Oxidation to a glycol by OsO4)

*H2O2 or N-methylmorpholine N-oxide (NMO) can be used to reoxidize OsO4

49
Q

Ozonolysis - Oxidative Cleavage (Alkene)

A

Ozonolysis - Oxidative Cleavage (Alkene)

*DMS or NaHCO3 can be used in step 2

50
Q

Hydrogenation (Alkene)

A

Hydrogenation (Alkene):

Catalytic reduction

Addition of H2

51
Q

Allylic Bromination (Alkene)

A

Allylic Bromination (Alkene):

*Radical intermediate

52
Q

HBr addition to Alkene under radical conditions

A

HBr addition to Alkene under radical conditions:

Anti-Markovnikov

Radical

53
Q

Oxidation of Alkenes by peroxycarboxylic acid

54
Q

Acidity of terminal Alkyne

A

Acidity of terminal Alkyne:

*Strong bases like NaNH2, NaH, or lithium diisopropylamine (LDA)

55
Q

Alkylation of acetylide anions.

A

Alkylation of acetylide anions.

Will displace halide from methyl or 1° haloalkane

56
Q

Synthesis of an alkyne from an alkene

A

Synthesis of an alkyne from an alkene

57
Q

Addition of Br2 or Cl2 (Alkyne)

A

Addition of Br2 or Cl2 (Alkyne)

Is anti slective

58
Q

Addition of HBr (Alkyne)

A

Addition of HBr (Alkyne):
Markovnikov addition of one HBr, second HBr forms germinal dihaloalkane.

59
Q

Keto-enol tautomerism (Alkyne)

60
Q

Hydroboration-oxidation (Alkyne)

BH3

A

Hydroboration-oxidation (Alkyne)

BH3

61
Q

Hydroboration-oxidation (Alkyne)

sia2

A

Hydroboration-oxidation (Alkyne)

sia2

62
Q

Hydration: Acid-catalyzed (Alkyne)

A

Hydration: Acid-catalyzed (Alkyne)

63
Q

Hydrogenation: Catalytic reduction (Alkyne)

Pd, Pt, or Ni

A

Hydrogenation: Catalytic reduction (Alkyne)

Pd, Pt, or Ni

64
Q

Hydrogenation: Catalytic reduction (Alkyne)

Lindar’s Catalyst (cis)

A

Hydrogenation: Catalytic reduction (Alkyne)

Lindar’s Catalyst (cis)

65
Q

Hydrogenation: Catalytic reduction (Alkyne)

2 Na, NH3 (trans)

A

Hydrogenation: Catalytic reduction (Alkyne)

2 Na, NH3 (trans)

66
Q

Electrophilic addition to conjugated diene

HBr

A

Electrophilic addition to conjugated diene

HBr

67
Q

Diels-Alder

A

Diels-Alder

68
Q

Halogenation (Electrophilic Aromatic Substitution)

FeCl3 or AlCl3

A

Halogenation (Electrophilic Aromatic Substitution)

FeCl3 or AlCl3

69
Q

Halogenation (Electrophilic Aromatic Substitution)

FeBr3 or AlBr3

A

Halogenation (Electrophilic Aromatic Substitution)

FeBr3 or AlBr3

70
Q

Nitrogenation: NO2 (Electrophilic Aromatic Substitution)

A

Nitrogenation: NO2 (Electrophilic Aromatic Substitution)

71
Q

Nitrogenation: NH2 (Electrophilic Aromatic Substitution)

A

Nitrogenation: NH2 (Electrophilic Aromatic Substitution)

72
Q

Sulfonation (Electrophilic Aromatic Substitution)

A

Sulfonation (Electrophilic Aromatic Substitution)

*Process is reversible with H2O, heat, and catalytic H2SO4

73
Q

Friedel-Crafts Alkylation (Electrophilic Aromatic Substitution)

A

Friedel-Crafts Alkylation (Electrophilic Aromatic Substitution)

74
Q

Friedel-Crafts Acylation (Electrophilic Aromatic Substitution)

A

Friedel-Crafts Acylation (Electrophilic Aromatic Substitution)

75
Q

(Electrophilic Aromatic Substitution)

Any Cation Intermediate

A

(Electrophilic Aromatic Substitution)

Anything that proceeds through cation intermediate can add to benzene ring.

76
Q

Grignard (Carbonyls)

A

Grignard (Carbonyls)

77
Q

Organolithium (Carbonyls)

A

Organolithium (Carbonyls)

78
Q

Terminal Alkyne (Carbonyls)

A

Terminal Alkyne (Carbonyls)

79
Q

Formation of Cynohydrin (Carbonyls)

A

Formation of Cynohydrin (Carbonyls)

80
Q

Wittig Reaction (Carbonyls)

A

Wittig Reaction (Carbonyls)

81
Q

Hydration (Carbonyls)

A

Hydration (Carbonyls)

82
Q

Hemiactal Formation (Carbonyls)

83
Q

Acetal Formation (Carbonyls)

A

Acetal Formation (Carbonyls)

*formed by dry acid. Reversible with aqueous acid.

84
Q

Imine Formation (Carbonyls)

A

Imine Formation (Carbonyls)

85
Q

Enamine Formation (Carbonyls)

A

Enamine Formation (Carbonyls)

86
Q

Hydrazone (Carbonyls)

A

Hydrazone (Carbonyls)

87
Q

Tollens Reagent (Carbonyls)

A

Tollens Reagent (Carbonyls)

*test for aldehyde, gives silver mirror

88
Q

Selective Reduction (Carbonyls)

LiAlH4 or NaBH4

A

Selective Reduction (Carbonyls)

*both LiAlH4 and NaBH4 will do this reaction

89
Q

Catalytic Reduction (Carbonyls)

Pt/H2

A

Catalytic Reduction (Carbonyls)

*will reduce other functionality

90
Q

Reductive Amination (Carbonyls)

A

Reductive Amination (Carbonyls)

91
Q

Clemmensen Reduction (Carbonyls)

A

Clemmensen Reduction (Carbonyls)

92
Q

Wolff-Kishner Reduction (Carbonyls)

A

Wolff-Kishner Reduction (Carbonyls)

Chemistry (5 decks)

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