Sn2 and Sn1 reactions – Flashcards

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