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REACTIONS Flashcards

1
Q

Draw out the mechanism for halohydrin formation

A

refer to notes

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1
Q

product of dihydroxylation

A

vicinal diols aka glycol (alcohol attachments on adjacent carbons)

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1
Q

What factor determines the rate of SN1 reactions?

A

electronics- the stability of the carbocation

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2
Q

hydroboration/oxidation of alkynes is markov? non markov?

A

non markovnikov

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2
Q

What happens to stereochemistry in an SN1 reaction?

A

stereochemistry is lost (since there’s a 50-50 chance of the Nu attaching to a particular side) and so you must draw both enantiomers or indicate that the product is a racemic mixture

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3
Q

reagents of free radical halogenation of alkanes

A

Br2or Cl2 and heat or light

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3
Q

product of dissolving metal reduction

A

alkene

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3
Q

reagents of catalytic hydrogenation with lindlar’s catalyst

A

H2

Pd poisoned with Pb

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4
Q

halogenation of alkynes results in syn? anti?

A

anti

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5
Q

Draw out the mechanism for hydroboration/oxidation of alkynes

A

refer to notess

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6
Q

What happens to stereochemistry in an SN2 reaction?

A

stereochemistry is inverted

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7
Q

What factor largely determines the rate of SN2 reactions?

A

steric hindrance

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8
Q

product of hydrohalogenation of alkenes

A

haloalkane

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8
Q

products of acid-catalyzed hydration of alkynes

A

enol and ketone

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8
Q

What reaction is acid-catalyzed hydration of alkynes analogous to?

A

oxymercuration of alkenes

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8
Q

Are 3° haloalkanes are more likely to react by SN1 or SN2? YYY

A

SN1; 3° haloalkanes make very stable carbocations and are protected from backside attack, preventing SN2

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9
Q

What 3 reactions form haloalkanes (an alkane with one halogen attachment)?

A

hydrohalogenation of alkenes, HBR addition to alkenes under radical conditions, and free radical halogenation of alkanes

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9
Q

intermediate of allylic bromination

A

allyl radical

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9
Q

product of catalytic hydrogentation with lindlar’s catalyst

A

alkene

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10
Q

Draw out the mechanism for oxymercuration/reduction.

A

refer to notes

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11
Q

Oxymercuration/reduction results in anti? syn? addition

A

anti

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13
Q

Which of the 3 reactions that form alcohols is carbocation rearrangement/1,2 hydride shifts possible?

A

acid-catalyzed hydration of alkenes

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14
Q

What happens in an SN2 reaction?

A

Nu attacks from the backside; bond between carbon and Lv breaks and bond between carbon and Nu forms at the same time

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16
Q

hydroboration/oxidation is Markov? non Markov?

A

non non non nan nan nan nan

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16
Q

halogenation of alkenes results in syn? anti?

A

anti

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17
Q

intermediate of halogenation of alkynes

A

bridged halogen ion

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19
Q

intermediate of oxymercuration/reduction

A

bridged mercurinium ion

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20
Q

Draw the transition state of an SN2 reaction.

A

refer to notes

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21
Q

Draw out the mechanism of acid-catalyzed hydration of alkynes

A

refer to notes

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22
Q

product of acid-catalyzed hydration of alkenes

A

alcohols

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23
Q

products of hydroboration/oxidation of alkynes

A

internal alkynes: ketone and enol

terminal alkynes: aldehyde and enol

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23
Q

Why is an SN2 reaction called so?

A

because both the Nu and the Lv ae involved in the rate determining step

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23
Q

List carbocations from least stable to most stable (for SN1 considerations)

A

methyl < 1° alkyl < 2° alkyl, 1° allylic, 1° benzylic < 3° alkyl, 2° allylic, 2° benzylic < 3° allylic, 3°benzylic

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25
Q

reagents of oxymercuration/reduction

A
  1. Hg(OAc)2, H2O
  2. NaBH4
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26
Q

intermeidate in halogenation of alkenes

A

bridged halogen ion

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27
Q

reagents of allylic bromination

A

NBS, light

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28
Q

reagents of hydroboration/oxidation of alkynes

A
  1. BH3, THF (or (sia)2BH if you just want one hydroboration step)
  2. H2O2, NaOH
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29
Q

product(s) of oxymercuration/reduction

A

alcohols

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30
Q

Which of the 3 reactions that form alcohols is non-Markovnikov?

A

hydroboration/oxidation of alkenes

31
Q

Free radical halogenation of alkanes is regioselective in the order ___ and ___ is more regioselective than ___.

A

3°>2°>1°

chlorine

bromine

32
Q

Draw out the mechanism for free radical halogenation of alkanes

A

refer to notes

34
Q

intermediate of hydrohalogenation of alkynes

A

vinylic carbocation (positive charge on one of the carbons of a carbon-carbon double bond)

34
Q

reagents of ozonolysis

A
  1. O3
  2. (CH3)2S aka DMS
35
Q

Oxymercuration/reduction is markov?antimarkov?

36
Q

product of catalytic hydrogenation of alkenes and alkynes

37
Q

What 3 reactions form aldehydes and ketones?

A

ozonolysis, acid-catalyzed hydration of alkynes, and hydroboration/oxidation of alkynes

39
Q

acid-catalyzed hydration is Markov or non-Markov?

A

Markovnikov

40
Q

What 3 reactions form alcohols?

A

hydroboration/oxidation of alkenes, acid-catalyzed hydration of alkenes, oxymercuration/reduction

41
Q

catalytic hydrogenation with linlar catalst results in syn? anti? addition

43
Q

Draw out the mechanism for hydrohalogenation of alkenes

A

refer to notes

44
Q

product of hydrohalogenation of alkynes

A

haloalkene with halogen on more substituted carbon

geminal dihaloalkane, with 2 halogen atoms on the most substituted carbon

45
Q

draw out the mechanism for dissolving metal reduction

A

refer to the book cuz you never wrote it down

47
Q

Draw out the mechanism for dihydroxylation

A

refer to notes

48
Q

product of halogenation of alkynes

A

1 mole of molecular halogen = vicinal dihaloalkene

2 moles of molecular halogen = vicinal tetrahaloalkane

49
Q

In halohydrin formation, OH goes on the ___ carbon, and X2 goes on the ___ carbon.

A

more substituted

50
Q

What are the 2 ways to form alkenes?

A

dissolving metal reduction, catalytic hydrogenation with lindlar catalyst

51
Q

dihydroxylation results in syn? anti?

52
Q

reagents of acid-catalyzed hydration of alkenes

A

H2O and H2SO4

54
Q

reagents of hydroboration/oxidaation

A
  1. BH3
  2. H2O2, NaOH
55
Q

intermediate that forms in acid-catalyzed hydration of alkenes

A

carbocation

56
Q

dissolving metal reduction results in syn? anti? addition

A

anti additon of hydrogens

57
Q

reagents of acid-catalyzed hydration of alkynes

A

H2O, H2SO4, HgSO4

58
Q

What are the 2 reactions that form alkynes?

A

alkylation of acetylide anions, dehydrohalogenation

59
Q

reagents of dissolving metal reduction

61
Q

reagents of hydrohalogenation of alkynes

62
Q

intermediate of hydrohalogenation of alkenes

A

carbocation intermediate; rearrangements are possible

62
Q

product of halogenation of alkenes

A

vicinal dihaloalkanes

63
Q

hydroboration/oxidation of alkynes results in syn? anti?

64
Q

halohydrin formation results in syn? anti? addition

A

anti addition

64
Q

reagents of halogenation of alkenes

A

X2, CH2Cl2

65
Q

Draw out the mechanism for ozonolysis

A

refer to notes

67
Q

Draw out the mechanism of acid-catalyzed hydration of alkenes.

A

refer to notes

68
Q

Draw out the mechanism for the hydrohalogenation of alkynes

A

refer to notes

70
Q

hydrohalogenation of alkynes is markov? non markov?

A

Markovnikov

71
Q

product of free radical halogenation of alkanes

A

haloalkanes

73
Q

Which of the 3 reactions that form alcohols is Markovnikov?

A

acid-catalyzed hydration of alkenes, oxymercuration/reduction

74
Q

Which of the 3 reactions that form alcohols forms a racemic mixture?

A

hydroboration/oxidation of alkenes, oxymercuration/reduction

76
Q

acid-catalyzed hydration of terminal alkynes is markov? anti markov?

A

markovnikov

77
Q

product of ozonolysis

A

carbon-carbon double bond is cleaved and an oxygen bandaid is put on each wound

79
Q

intermediates of acid-catalyzed hydration of alkynes

A

bridged mercurinium ion

80
Q

Catalytic hydrogenation results in syn? anti? addition

81
Q

reagents of halogenation of alkynes

A

2 mol X2, CH2Cl2

82
Q

intermediates of ozonolysis

A

molozonoide, which rearranges to ozonoide

83
Q

Draw out the mechanism for allylic bromination.

A

refer to notesss

84
Q

product of hydroboration/oxidation of alkenes

85
Q

Why is an SN1 reaction called so?

A

because only 1 species- the haloalkane- is involved in the rate determining step

87
Q

Draw out the mechansim for hydroboration/oxidation of alkenes.

A

refer to notes

88
Q

reagents of halohydrin formation

89
Q

draw out the mechanism for the halogenation of alkynes

A

refer to notes

90
Q

reagents of hydrohalogenation of alkenes

91
Q

hydrohalogenation of alkenes is markov? or non-markov?

A

markovnikov

92
Q

hydroboration/oxidation results in syn? anti? addition

A

syn, since C-B and C-H bonds form simultaneously

93
Q

reagents of dihydroxylation

A
  1. OsO4
  2. NaHSO3/H2O
94
Q

reagents of catalytic hydrogenation of alkenes and alkynes

A

H2

Pd, Pt, Ni, some metal catalyst

2 mol of H2 if starting from an alkyne

95
Q

What happens in an SN1 reaction?

A

bond between C and Lv is broken completely

carbocation intermediate is formed and molecule becomes trigonal planar

Nu attacks from either side

racemic mixture is formed

96
Q

Draw out the mechanism for halogenation of alkenes

A

refer to notes

97
Q

intermediate of halohydrin formation

A

bridged halogen ion

Chem 30A (10 decks)

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