Chemistry 2510- Midterm 2 Osu Organic
Chemistry Questions and Answers.
The bond strength of C-X decreases as - Answer size of X increases
F>Cl>Br>I
bond dissociation
The bond between carbon and halogen is made up of an - Answer sp3 orbital on carbon and a
p orbital of the halogen
Short bonds are stronger than - Answer longer bonds
Boiling points of haloalkanes are generally higher than - Answer corresponding alkanes; due to
dipole dipole interactions
Boiling points also rise with increasing - Answer size of the halogen
polarizability - Answer degree to which the electron cloud is able to deform
nucleophile - Answer substances that contain an unshared electron pair
Nucleophilic substitution - Answer reagent attacks the haloalkane and replaces the halide
Negatively charged nucleophile reacts with a haloalkane to yield - Answer a neutral
substitution product
An uncharged nucleophile yields - Answer a positively charged substitution product( with the
counteranion it becomes a salt)
substrate - Answer starting organic material
Bimolecular Nucleophilic Subsitution - Answer two reactants interact in one step
nucleophile attacks substrate with simultaneous expulsion of the leaving group
Sn2 is a - Answer concerted reaction
, backside displacement - Answer the nucleophile approaches the carbon from the side
opposite the leaving group
Inversion of Configuration - Answer occurs with all Sn2 reactions
S goes to R, R goes to S
Stereospecific - Answer a process whose mechanism requires that each stereoisomer of the
starting material transform into a specific stereoisomer
As the nucleophile approaches the back lobe of the sp3 hybrid orbital used by the carbon to
bind to the halogen, the rest of the molecule becomes - Answer planar at the transition state
by changing the hybridization to sp2.
Double inversion sequence of two Sn2 processes gives - Answer desired product(if you want to
maintain the same configuration); retention of configuration
Facility of Sn2 reactions depend on several factors - Answer -nature of leaving group
-reactivity of nucleophile
-and the structure of the alkyl portion of the substrate
Leaving group ability is correlated with - Answer its capacity to accommodate a negative
charge
For halogens, leaving group ability increase - Answer down the column
Sulfur Derivatives are also good - Answer leaving groups
ROSO3- and RSO3-
Leaving group ability is inversely related to - Answer base strength
Weak bases are the best - Answer to accommodate negative charge and are the best leaving
groups
Good leaving groups are the - Answer conjugate bases of strong acids
Chemistry Questions and Answers.
The bond strength of C-X decreases as - Answer size of X increases
F>Cl>Br>I
bond dissociation
The bond between carbon and halogen is made up of an - Answer sp3 orbital on carbon and a
p orbital of the halogen
Short bonds are stronger than - Answer longer bonds
Boiling points of haloalkanes are generally higher than - Answer corresponding alkanes; due to
dipole dipole interactions
Boiling points also rise with increasing - Answer size of the halogen
polarizability - Answer degree to which the electron cloud is able to deform
nucleophile - Answer substances that contain an unshared electron pair
Nucleophilic substitution - Answer reagent attacks the haloalkane and replaces the halide
Negatively charged nucleophile reacts with a haloalkane to yield - Answer a neutral
substitution product
An uncharged nucleophile yields - Answer a positively charged substitution product( with the
counteranion it becomes a salt)
substrate - Answer starting organic material
Bimolecular Nucleophilic Subsitution - Answer two reactants interact in one step
nucleophile attacks substrate with simultaneous expulsion of the leaving group
Sn2 is a - Answer concerted reaction
, backside displacement - Answer the nucleophile approaches the carbon from the side
opposite the leaving group
Inversion of Configuration - Answer occurs with all Sn2 reactions
S goes to R, R goes to S
Stereospecific - Answer a process whose mechanism requires that each stereoisomer of the
starting material transform into a specific stereoisomer
As the nucleophile approaches the back lobe of the sp3 hybrid orbital used by the carbon to
bind to the halogen, the rest of the molecule becomes - Answer planar at the transition state
by changing the hybridization to sp2.
Double inversion sequence of two Sn2 processes gives - Answer desired product(if you want to
maintain the same configuration); retention of configuration
Facility of Sn2 reactions depend on several factors - Answer -nature of leaving group
-reactivity of nucleophile
-and the structure of the alkyl portion of the substrate
Leaving group ability is correlated with - Answer its capacity to accommodate a negative
charge
For halogens, leaving group ability increase - Answer down the column
Sulfur Derivatives are also good - Answer leaving groups
ROSO3- and RSO3-
Leaving group ability is inversely related to - Answer base strength
Weak bases are the best - Answer to accommodate negative charge and are the best leaving
groups
Good leaving groups are the - Answer conjugate bases of strong acids
