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
The benefits of buying summaries with Stuvia:
Guaranteed quality through customer reviews
Stuvia customers have reviewed more than 700,000 summaries. This how you know that you are buying the best documents.
Quick and easy check-out
You can quickly pay through credit card for the summaries. There is no membership needed.
Focus on what matters
Your fellow students write the study notes themselves, which is why the documents are always reliable and up-to-date. This ensures you quickly get to the core!
Frequently asked questions
What do I get when I buy this document?
You get a PDF, available immediately after your purchase. The purchased document is accessible anytime, anywhere and indefinitely through your profile.
Satisfaction guarantee: how does it work?
Our satisfaction guarantee ensures that you always find a study document that suits you well. You fill out a form, and our customer service team takes care of the rest.
Who am I buying these notes from?
Stuvia is a marketplace, so you are not buying this document from us, but from seller lectknancy. Stuvia facilitates payment to the seller.
Will I be stuck with a subscription?
No, you only buy these notes for $12.49. You're not tied to anything after your purchase.
