Sn2 and Sn1 reactions

weak nucleophiles are OK
sn1
strong nucleophile needed
sn2
3 > 2
sn1
CH3X> 1> 2
sn2
good ionizing solvent needed
sn1
wide variety of solvents, like to be less polar
sn2
good leaving group required
sn1 and sn2
AgNO3 forces ionization
sn1
first order reaction
sn1
second order reaction
sn2
mixture of inversion and retention
sn1
complete inversion
sn2
common rearrangements
sn1
impossible to have rearrangements
sn2
2-chloro-2-methylbutane + CH3COOH
sn1
isobutyl bromide + sodium methoxide
sn2
1-iodo-1methylcyclohexane + ethanol
sn1
cyclohexyl bromide + methanol
sn1
cyclohexyl bromide + sodium ethoxide
sn2
1-bromopentane will react faster by sn1 than 2-bromopentane t/f
false
2-bromo-2-methylbutane will react faster by sn1 than 2-bromo-3-methylbutane t/f
true
1-bromo-2,2-dimethylpropane will react faster than 2-bromopropane by sn1 t/f
false -CHECK!
tert-butyl chloride will react faster by sn1 than 2-iodo-2-methylbutane t/f
false- iodine better leaving group both are 3
2-bromo-2-methylbutane will react faster by sn1 than ethyl iodide t/f
true
(CH3CH2)3N is a stronger nucleophile than (CH3CH2)2NH
false – more hindered
NH3 is a stronger nucleophile than PH3
false- more electronegative, less large
(CH3)2O is a stronger nucleophile than (CH3)2S
false- more electronegative, less large
CH3S- is a stronger nucleophile than H2S
true
(CH3)3N is a stronger nucleophile than (CH3)2O
true- N is less electronegative
only consider steric hinderence when dealing with the same molecules t/f
true
what to consider w nucleophiles that contain different atoms:
electronegativity and largeness
CH3COO- is a stronger nucleophile than CF3COO-
true- the elecetrons are less delocalized. the electrons want to be available and exposed
(CH3)2CHO- is a stronger nucleophile than CH3CH2CH2O-
false- more hindered
I- is a stronger nucleophile than Cl-
true- it is less electronegative
2-methy-1-iodopropane is a better sn2 substrate than tert-butyl iodine
true
cyclohexyl bromide is a better sn2 substrate than 1-bromo-1-methylcyclohexane
true
2-bromobutane is a better sn2 substrate than isopropyl bromide
false- no substituent on neighboring carbon
1-chloro-2,2-dimethylbutane is a better sn2 substrate than 2-chlorobutane
false
1-iodobutane is a better sn2 substrate than 2-iodopropane
true
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