stupid Flashcards
1
Q
strong base, weak nucleophile
A
NaH, DBU, DBN, tBuko-
2
Q
strong base, strong nucleophile
A
OH-, OMe-, OEt-
3
Q
weak base, strong nucleophile
A
I-, Br-, Cl-, RS-, HS-, RSH, H2S, NC-
4
Q
weak base weak nucleophile
A
H20, MeOH, EtOH
5
Q
what type of rxn: strong base weak nuc
A
1-E2
2-E2
3-E2
6
Q
what type of rxn: strong base strong nuc
A
1-E2/ SN2 MAJOR
2-E2 MAJOR/ SN2
3-E2
7
Q
what type of rxn: weak base, strong nuc
A
1-SN2
2-SN2
3-SN1
8
Q
what type of rxn: weak base weak nuc
A
1-
2
3- SN1 MAJOR/ E1
9
Q
PKA OF PROTONATED ALCHOHOL
A
<0
10
Q
PKA OF PROTONATED CARBOXYLLIC ACID
A
<0
11
Q
PKA OF PROTONATED WATER
A
<0
12
Q
PKA OF CARBOXYLLIC ACID
A
5
13
Q
PKA OF R2NH
A
40
14
Q
PKA OF SP3 CARBON
A
60
15
Q
PKA OF PROTONATED AMINE RNH3+
A
10
16
Q
PKA OF ALCOHOL
A
15
17
Q
PKA OF WATER
A
15
18
Q
PKA OF ALKENE
A
25
19
Q
PKA OF SP2 CARBON
A
40
20
Q
PKA OF R3NH+
A
10
21
Q
Will you get a good grade on this exam?
A
inshallah
22
Q
anti or syn: acid catalyzed hydration of alkenes
A
anti and syn
23
Q
a or s: addition of alchohol
A
anti and syn
24
Q
is a carbocation formed in the oxymercuration reaction
A
no
25
is oxymercuration a markovnikov product
yes
26
is hydroboration markovnikov
no
27
does hydroboration produce a carbocation
no
28
a or s: hydroboration
syn
29
do halogen additions produce a carbocation
no
30
a or s: halogen additions
anti
31
does halohydrin addition to alkene make a carbocation
no
32
a or s: halohydrin addition
anti and also formed vicinal halide
33
a or s: addition of H-X
anti and syn
34
what is a peroxyacid
mCPBA
35
what is the product of a peroxyacid addition to an alkene
syn addition of epoxide
36
does ozonolysis produce a carboaction
no
37
does a carbocation form in alkene reaction with water and acid
yes
38
does carbocation form with water addition to alkynes
no
39
how do you get the ketone group on the end of a terminal alkyne
by using R2BH/THF and H20,H202,OH-
40
how do you get the ketone group on the second last end of terminal alkyne
by using H2O, H2SO4, HGSO4
41
what does hydroboration/oxidation form
enol-keto
42
is hydroboration for alkenes concerted? anti or syn
it is concerted and it is syn
43
does lindlar catalyst make cis or trans
cis
44
how to get trans in alkene hydration
Na or Li and NH3
45
what does ozonolysis in alknes produce
carboxyllic acid
46
what is the rate in an SN2 reaction inversly proportional to
the size of the nucleophile and the size of the alkyl halide
47
what is POCl3 used for, does it form carbocation
alcohol dehydration reactions, it does not form carbocation
48
what reagent can you use to reduce an carbonyl group to an alxohol. does this give racemic products
1)LIAlH4, THF, H2O
2)NaBH4, MeOH
in many cases yes it does give racemic products
49
what does Na2Cr2O7 do to alcohols, what type (1,2,3)
oxidates them
50
what does Na2Cr2O7 turn primary alcohols into
carboxyllic acid
51
what does Na2Cr2O7 turn secondary alcohols into
ketones
52
how do you get a ketone in a primary alcohol
use PCC (CH2Cl2)
53
what does NaOCl do to alcohols
tunr them into ketones
54
what does swern oxidation turn primary alcohols into
aldehyde
55
what does swern oxidation turn secondary alcohols into
ketones
56
what do you use if you want a carboxyllic acid to form from a primary alcohol
Na2Cr2O7
57
what do you use if you want an aldehyde to form from a primary alcohol
swern oxidation
58
what do aprotic polar solvents prefer
stronger bases
59
what do protic polar solvents prefer
bigger atoms for increase polarizability
60
is acetone aprotic or protic
aprotic
61
is DMSO aprotic or protic
aprotic
62
is acetic acid (CH3COOH) aprotic or protic
PROTIC
63
is DMF aprotic or protic
APROTIC
64
is water aprotic or protic
PROTIC
65
are alcohols aprotic or protic
protic
66
what is the reuirement for secondary alchohols during protonation
heat
67
what is the product of protonation of an alcohol
an alkyl halide
68
do secondary and teriary alcohols undergo SN1 OR SN2 protonation
sn1 so carbocation is formed
69
do primary alcohols udnergo SN2 OR SN1 protonation of an alcohol
SN2
70
What is the lucas reagent (does it undergo SN1 OR SN2)
ZnCl2 (sn2)
71
what does ZnCl2 do
activates alcohols turning them into alkyl halides
72
what dose PBr3 do/// SN1 OR SN2// what degree of alcohol
it activates alcohols, SN2,, primary and secondary
73
what does SoCl2 do // what degree of alcohols can be used in this
activates alcohols, primary and secondary
74
what acid would you use for SN1 protonation of a teritary or secondary alcohol
HBR
75
what happens with SOCl2 and PBr3
inversion of stereochem
76
what are sulfonate esters
```
R
/
TsCl, TfCl, MsCl, 0=s=0
/
cl
```
77
how do sulfonate esters work
they attatch themselves as the leaving group
78
what process to ethers participate in
nucleophilic substitution reactions
79
do ethers undergo sn1 or sn1 nuc sub rxns
can be either depending on if a stable C+ can be formed
80
what carbon does the nucleophile attack in a ether nuc sub rxn
the less hindered carbon
81
what stereochemical outcome occurs during acidic and basic reactions with epoxides
inversion of stereochem
82
what carbon is attacked in an acidic epoxide reaction
more sub carbon
83
what carbon is attacked in a basic epoxide reaction
less sub carbon
84
what acid can you use for acidic epoxide reaction
HBr
85
what base can you use for basic epoxide reaction
CH2ONa
86
what is the oucome of an epoxide reaction
alchohol on one side and the neg charge speices on the other
87
how to get an elimination reaction to occur with an epoxide
only works with hindered epoxides and bases
88
how to turn an epoxide into a trans diol
use a strong base such as OH-
89
how to turn an epoxide into a cis diol
use OsO4 AND H2O2
90
what reactions do quat ammonium undergo
elimination reactions where the less sub alkene is favoured. The ammonium and what its attatched to seperate.
91
what type of elimination reaction do quat ammoninum undergo
E2
92
kinetic product
forms more rapidly
93
thermodynamic product
more stable product
94
what product is the 1,2 addition product
the kinetic
95
what product is the 1,4 addition product
the thermodynamic product
