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stupid Flashcards

1
Q

strong base, weak nucleophile

A

NaH, DBU, DBN, tBuko-

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2
Q

strong base, strong nucleophile

A

OH-, OMe-, OEt-

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3
Q

weak base, strong nucleophile

A

I-, Br-, Cl-, RS-, HS-, RSH, H2S, NC-

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4
Q

weak base weak nucleophile

A

H20, MeOH, EtOH

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5
Q

what type of rxn: strong base weak nuc

A

1-E2
2-E2
3-E2

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6
Q

what type of rxn: strong base strong nuc

A

1-E2/ SN2 MAJOR
2-E2 MAJOR/ SN2
3-E2

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7
Q

what type of rxn: weak base, strong nuc

A

1-SN2
2-SN2
3-SN1

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8
Q

what type of rxn: weak base weak nuc

A

1-
2
3- SN1 MAJOR/ E1

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9
Q

PKA OF PROTONATED ALCHOHOL

A

<0

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10
Q

PKA OF PROTONATED CARBOXYLLIC ACID

A

<0

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11
Q

PKA OF PROTONATED WATER

A

<0

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12
Q

PKA OF CARBOXYLLIC ACID

A

5

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13
Q

PKA OF R2NH

A

40

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14
Q

PKA OF SP3 CARBON

A

60

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15
Q

PKA OF PROTONATED AMINE RNH3+

A

10

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16
Q

PKA OF ALCOHOL

A

15

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17
Q

PKA OF WATER

A

15

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18
Q

PKA OF ALKENE

A

25

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19
Q

PKA OF SP2 CARBON

A

40

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20
Q

PKA OF R3NH+

A

10

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21
Q

Will you get a good grade on this exam?

A

inshallah

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22
Q

anti or syn: acid catalyzed hydration of alkenes

A

anti and syn

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23
Q

a or s: addition of alchohol

A

anti and syn

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24
Q

is a carbocation formed in the oxymercuration reaction

A

no

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25
Q

is oxymercuration a markovnikov product

A

yes

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26
Q

is hydroboration markovnikov

A

no

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27
Q

does hydroboration produce a carbocation

A

no

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28
Q

a or s: hydroboration

A

syn

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29
Q

do halogen additions produce a carbocation

A

no

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30
Q

a or s: halogen additions

A

anti

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31
Q

does halohydrin addition to alkene make a carbocation

A

no

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32
Q

a or s: halohydrin addition

A

anti and also formed vicinal halide

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33
Q

a or s: addition of H-X

A

anti and syn

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34
Q

what is a peroxyacid

A

mCPBA

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35
Q

what is the product of a peroxyacid addition to an alkene

A

syn addition of epoxide

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36
Q

does ozonolysis produce a carboaction

A

no

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37
Q

does a carbocation form in alkene reaction with water and acid

A

yes

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38
Q

does carbocation form with water addition to alkynes

A

no

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39
Q

how do you get the ketone group on the end of a terminal alkyne

A

by using R2BH/THF and H20,H202,OH-

40
Q

how do you get the ketone group on the second last end of terminal alkyne

A

by using H2O, H2SO4, HGSO4

41
Q

what does hydroboration/oxidation form

A

enol-keto

42
Q

is hydroboration for alkenes concerted? anti or syn

A

it is concerted and it is syn

43
Q

does lindlar catalyst make cis or trans

A

cis

44
Q

how to get trans in alkene hydration

A

Na or Li and NH3

45
Q

what does ozonolysis in alknes produce

A

carboxyllic acid

46
Q

what is the rate in an SN2 reaction inversly proportional to

A

the size of the nucleophile and the size of the alkyl halide

47
Q

what is POCl3 used for, does it form carbocation

A

alcohol dehydration reactions, it does not form carbocation

48
Q

what reagent can you use to reduce an carbonyl group to an alxohol. does this give racemic products

A

1)LIAlH4, THF, H2O
2)NaBH4, MeOH
in many cases yes it does give racemic products

49
Q

what does Na2Cr2O7 do to alcohols, what type (1,2,3)

A

oxidates them

50
Q

what does Na2Cr2O7 turn primary alcohols into

A

carboxyllic acid

51
Q

what does Na2Cr2O7 turn secondary alcohols into

A

ketones

52
Q

how do you get a ketone in a primary alcohol

A

use PCC (CH2Cl2)

53
Q

what does NaOCl do to alcohols

A

tunr them into ketones

54
Q

what does swern oxidation turn primary alcohols into

A

aldehyde

55
Q

what does swern oxidation turn secondary alcohols into

A

ketones

56
Q

what do you use if you want a carboxyllic acid to form from a primary alcohol

A

Na2Cr2O7

57
Q

what do you use if you want an aldehyde to form from a primary alcohol

A

swern oxidation

58
Q

what do aprotic polar solvents prefer

A

stronger bases

59
Q

what do protic polar solvents prefer

A

bigger atoms for increase polarizability

60
Q

is acetone aprotic or protic

A

aprotic

61
Q

is DMSO aprotic or protic

A

aprotic

62
Q

is acetic acid (CH3COOH) aprotic or protic

A

PROTIC

63
Q

is DMF aprotic or protic

A

APROTIC

64
Q

is water aprotic or protic

A

PROTIC

65
Q

are alcohols aprotic or protic

A

protic

66
Q

what is the reuirement for secondary alchohols during protonation

A

heat

67
Q

what is the product of protonation of an alcohol

A

an alkyl halide

68
Q

do secondary and teriary alcohols undergo SN1 OR SN2 protonation

A

sn1 so carbocation is formed

69
Q

do primary alcohols udnergo SN2 OR SN1 protonation of an alcohol

A

SN2

70
Q

What is the lucas reagent (does it undergo SN1 OR SN2)

A

ZnCl2 (sn2)

71
Q

what does ZnCl2 do

A

activates alcohols turning them into alkyl halides

72
Q

what dose PBr3 do/// SN1 OR SN2// what degree of alcohol

A

it activates alcohols, SN2,, primary and secondary

73
Q

what does SoCl2 do // what degree of alcohols can be used in this

A

activates alcohols, primary and secondary

74
Q

what acid would you use for SN1 protonation of a teritary or secondary alcohol

A

HBR

75
Q

what happens with SOCl2 and PBr3

A

inversion of stereochem

76
Q

what are sulfonate esters

A 
R 
                                  /
TsCl, TfCl, MsCl, 0=s=0
                                 /
                              cl
77
Q

how do sulfonate esters work

A

they attatch themselves as the leaving group

78
Q

what process to ethers participate in

A

nucleophilic substitution reactions

79
Q

do ethers undergo sn1 or sn1 nuc sub rxns

A

can be either depending on if a stable C+ can be formed

80
Q

what carbon does the nucleophile attack in a ether nuc sub rxn

A

the less hindered carbon

81
Q

what stereochemical outcome occurs during acidic and basic reactions with epoxides

A

inversion of stereochem

82
Q

what carbon is attacked in an acidic epoxide reaction

A

more sub carbon

83
Q

what carbon is attacked in a basic epoxide reaction

A

less sub carbon

84
Q

what acid can you use for acidic epoxide reaction

A

HBr

85
Q

what base can you use for basic epoxide reaction

A

CH2ONa

86
Q

what is the oucome of an epoxide reaction

A

alchohol on one side and the neg charge speices on the other

87
Q

how to get an elimination reaction to occur with an epoxide

A

only works with hindered epoxides and bases

88
Q

how to turn an epoxide into a trans diol

A

use a strong base such as OH-

89
Q

how to turn an epoxide into a cis diol

A

use OsO4 AND H2O2

90
Q

what reactions do quat ammonium undergo

A

elimination reactions where the less sub alkene is favoured. The ammonium and what its attatched to seperate.

91
Q

what type of elimination reaction do quat ammoninum undergo

A

E2

92
Q

kinetic product

A

forms more rapidly

93
Q

thermodynamic product

A

more stable product

94
Q

what product is the 1,2 addition product

A

the kinetic

95
Q

what product is the 1,4 addition product

A

the thermodynamic product

stupid orgo (7 decks)

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