alkyl halide - Answer-compounds in which a halogen is connected to an sp3 hybridized carbon atom
2 types of rxn's alkyl halides go under - Answer-substitution and elimination
substitution reaction - Answer-when treated with a nucleophile, the nucleophile replaces the halogen
elimination re...
Organic Chem Exam 3 Questions and
Answers
alkyl halide - Answer-compounds in which a halogen is connected to an sp3 hybridized
carbon atom
2 types of rxn's alkyl halides go under - Answer-substitution and elimination
substitution reaction - Answer-when treated with a nucleophile, the nucleophile replaces
the halogen
elimination reaction - Answer-when treated with a base, a pi bond will form creating an
alkene
what functions does the halogen serve in an alkyl halide - Answer-1) halogen withdraws
electron density leaving the carbon open to nucleophilic attack
2)halogen can serve as the leaving group
what are good leaving groups - Answer-conjugate bases of strong acids, halogens
serve as excellent leaving groups
alpha position - Answer-the carbon atom connected directly to the halogen
beta position - Answer-the carbon atoms connected to the alpha position can be up to 3
beta positions
organohalide - Answer-a more general term for any organic compound that contains a
halogen (includes aryl halides and vinyl halides)
how are organohalides useful - Answer-serve as excellent starting materials for more
complex molecules
Sn2 - Answer-bimolecular nucleophilic substitution with 2nd order kinetics
2 mechanisms of Sn2 - Answer-nucleophilic attack and loss of leaving group
stereospecific - Answer-the configuration of the product is dependent upon configuration
of the reaction
walden inversion - Answer-inversion of configuration, R to S, or S to R. due to back-side
attack
back-side attack - Answer-1) lone pairs of the leaving group create high regions of
electron density that block the front side
, 2) a node is present between the alpha carbon and halogen that blocks front side attack
how does alkyl halide structure effect rate - Answer-the presence of substituents at the
alpha or beta position significantly reduce rate
what effects rate reaction more, substituents on the alpha or beta position - Answer-
alpha
can Sn2 reactions be performed on tertiary alkyl halides - Answer-NO
will a Sn2 reaction proceed with 3 substituents on the beta position - Answer-technically
yes, but not at a practical rate
how does steric hinderance effect kinetics - Answer-more substituents increase steric
hinderance and increase the activation energy, and thus decrease reaction rate
nucleophilicity - Answer-The rate at which a nucleophile will attack a suitable
electrophile.
how do strong/weak nucleophiles effect reaction rate - Answer-strong nucleophiles give
a relatively fast Sn2 reaction, while weak nucleophiles give a relatively slow reaction, in
fact weak nucleophiles are generally too slow to be of practical use
what factors impact nucleophilicity - Answer-polarizability and charge
what kind of solvents do Sn2 reactions require - Answer-polar, since the nucleophile,
leaving group, and transition state are generally ionic
2 types of polar solvents - Answer-protic and aprotic
protic solvents - Answer-contain hydrogen atom connected directly to an
electronegative atom
aprotic solvents - Answer-lack a hydrogen atom connected directly to an electronegative
atom
reaction rate of Sn2 reactions with protic solvents vs aprotic solvents - Answer-Sn2
reactions generally much faster when performed in polar aprotic solvents
what is the pattern of reaction rate with protic solvents with halogen nucleophiles -
Answer-Iodine is the fastest, while fluorine is the slowest
what is the pattern of reaction rate with aprotic solvents with halogen nucleophiles -
Answer-fluorine is the fastest, while iodine is the slowest
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