Sign in to save your progress, vote, and build your own decks.Sign in
Organic Chemistry Test Prep I
33 cards·by Simiankolya
In a substitution reaction, the _ is attacked by the _
Electrophile, nucleophile
Sn2 reactions happen fastest on _ electrophiles; and barely occur at all on _ electrophiles
Primary, tertiary
Sn1 reactions happen fastest on _ electrophiles; and barely occur on _ electrophiles
Tertiary, primary
The first step of an Sn1 reaction is the loss of a _
Leaving group
The first step of a _ reaction is the loss of a leaving group
Sn1
Sn2 reactions occur most readily on primary electrophiles due to less _; Sn2 reactions prefer
tertiary electrophiles due to _
Steric hinderance, stability of charge
A weak nucleophile has a _ or _ charge
Neutral, positive
A moderate nucleophile has a _ charge, and is very _
Negative, stable
A strong nucleophile has a _ charge that is not _; and the charge is not on a _
Negative, stabilized, halogen
The "2" in "Sn2" means that the rate of reaction is dependent on the concentrations of the _ and
the _
Substrate, nucleophile
The "1" in "Sn1" means that the rate of reaction is dependent only on the concentration of the _
Substrate
An excellent leaving group does not have a _ charge
Negative
A good leaving group has a _ charge and is _
Negative, stable
A bad leaving group has a _ charge that is not _
Negative, stabilized
A _ reaction is much more sensitive to the stability of the leaving group than a _ reaction
Sn1, Sn2
For a leaving group to be neutral when it leaves, it must have a _ charge while it is still
attached to the molecule.
Positive
A bad leaving group can be converted into an excellent one by _ it
Protonating
Polar aprotic solvents favor _ reactions
Sn2
_ solvents favor Sn2 reactions
Polar aprotic
Sn1 reactions need a _ solvent to stabilize the carbocation
Polar
_ reactions need a polar solvent to stabilize the carbocation
Sn1
Sn2 reactions need a _ solvent to dissolve the nucleophile
Polar
Sn2 reactions need a polar solvent to dissolve the _
Nucleophile
The most common polar aprotic solvents are _, _, _, and _
Acetone, DMSO, DME, DMF
Acetone, DMSO, DME, and DMF are all _ solvents
Polar aprotic
A nucleophile with a _ charge, when dissolved in a polar solvent, will be surrounded by
asolvent shell
Negative
A nucleophile with a negative charge, when dissolved in a polar solvent, will be surrounded by
a _
Solvent shell
Nucleophiles are always hindered by a solvent shell, except when they are in a _ solvent
Polar aprotic
Sn2 reactions performed with nucleophiles in polar aprotic solvents occur about _ times
faster than in regular protic solvents
1000
Sn2 reactions _ the stereocenter
Invert
Sn1 reactions produce _ mixtures
Racemic
Sn2 reactions need a good, _ nucleophile and a _ ion such as Na or K
Anionic, metal
In an Sn1 reaction, there is a _ solvent, which can also serve as the _; this is called _
Protic, nucleophile, solvolysis